Download PDF
Synthesis 2008(24): 3877-3902  
DOI: 10.1055/s-0028-1083256
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

One-Pot Cyclizations of (2,4-Dioxobutylidene)phosphoranes and (2-Alkoxy-4-oxobut-2-enylidene)phosphoranes

Holger Feista, Peter Langer*a,b
a Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany
Fax: +49(381)4986412; e-Mail: peter.langer@uni-rostock.de;
b Leibniz-Institut für Katalyse e. V. , Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany
Further Information

Publication History

Received 1 July 2008
Publication Date:
01 December 2008 (online)

    Permissions and Reprints All articles of this category

Abstract

(2,4-Dioxobutylidene)phosphoranes and (2-alkoxy-4-oxobut-2-enylidene)phosphoranes are readily available and represent versatile building blocks in one-pot cyclizations. Their reactions with various electrophiles, such as 1,3-dicarbonyl compounds, enones, α-halo ketones, or hydrazine derivatives, allow a convenient synthesis of a variety of carbocyclic and heterocyclic ring systems.

1 Introduction

2 (2,4-Dioxobutylidene)phosphoranes

2.1 Synthesis

2.2 Cyclization Reactions

2.2.1 Formation of Five-Membered Carbacycles

2.2.2 Formation of Six-Membered Carbacycles

2.2.3 Formation of Seven-Membered Carbacycles

2.2.4 Formation of Heterocycles

3 (2-Alkoxy-4-oxobut-2-enylidene)phosphoranes

3.1 Synthesis

3.2 Cyclization Reactions

3.2.1 Five-Membered Rings

4 Summary

Key words

arenes - cyclizations - one-pot reactions - heterocycles - phosphoranes

    References

  • For reviews of Wittig reactions, see:
  • 1a Bestmann HJ. Klein O. In Houben-Weyl Methoden der organischen Chemie   Vol. 5/1b:  Mueller E. Thieme; Stuttgart: 1972.  p.383 
    Google Scholar
  • 1b Maryanoff BE. Reitz AB. Chem. Rev.  1989,  89:  863 
    Google Scholar
  • 1c Abell AD. Edmonds MK. Organophosphorus Reagents   Murphy P. Oxford University Press; Oxford UK: 2004.  p.99 
    Google Scholar
  • 1d Vedejs E. Peterson MJ. Advances in Carbanion Chemistry   Vol. 2:  JAI Press; New York: 1996.  p.1 
    Google Scholar
  • 1e Vedejs E. Peterson MJ. Top. Stereochem.  1994,  21:  1 
    Google Scholar
  • 2a Tietze LF. Beifuss U. Angew. Chem., Int. Ed. Engl.  1993,  32:  137 
    Google Scholar
  • 2b Tietze LF. Chem. Rev.  1996,  96:  115 
    Google Scholar
  • 2c Tietze LF. Brasche G. Gericke KM. Domino Reactions in Organic Synthesis   Wiley-VCH; Weinheim: 2006. 
    Google Scholar
  • 3a Patre RE. Gawas S. Sen S. Parameswaran PS. Tilve SG. Tetrahedron Lett.  2007,  48:  3517 
    Google Scholar
  • 3b Varseev GN. Maier ME. Org. Lett.  2007,  9:  1461 
    Google Scholar
  • 3c Wu J. Sun L. Dai W.-M. Tetrahedron  2006,  62:  8360 
    Google Scholar
  • 3d Jarosz S. Szewczyk K. Tetrahedron Lett.  2001,  42:  3021 
    Google Scholar
  • 3e Jarosz S. Skóra S. Tetrahedron: Asymmetry  2000,  11:  1425 
    Google Scholar
  • 3f Jarosz S. Skóra S. Tetrahedron: Asymmetry  2000,  11:  1433 
    Google Scholar
  • 3g Jarosz S. J. Chem. Soc., Perkin Trans. 1  1997,  3579 
    Google Scholar
  • 4a Herdeis C. Küpper P. Plé S. Org. Biomol. Chem.  2006,  4:  524 
    Google Scholar
  • 4b Herdeis C. Telser J. Eur. J. Org. Chem.  1999,  1407 
    Google Scholar
  • 4c Herdeis C. Schiffer T. Synthesis  1997,  1405 
    Google Scholar
  • 5a Blanco G. Quintela JM. Peinador C. Tetrahedron  2007,  63:  2034 
    Google Scholar
  • 5b Zhao J.-F. Xie C. Xu S.-Z. Ding M.-W. Xiao W.-J. Org. Biomol. Chem.  2006,  4:  130 
    Google Scholar
  • 5c Yuan J.-Z. Fu B.-Q. Ding M.-W. Yang G.-F. Eur. J. Org. Chem.  2006,  4170 
    Google Scholar
  • 5d Ding M.-W. Huang N.-Y. He H.-W. Synthesis  2005,  1601 
    Google Scholar
  • 5e Ding M.-W. Chen Y.-F. Huang N.-Y. Eur. J. Org. Chem.  2004,  3872 
    Google Scholar
  • 5f Ding M.-W. Fu B.-Q. Cheng L. Synthesis  2004,  1067 
    Google Scholar
  • 5g Wang H.-Q. Liu Z.-J. Yang L.-M. Ding M.-W. J. Heterocycl. Chem.  2004,  41:  393 
    Google Scholar
  • 5h Molina P. Fresneda PM. Delgado S. Bleda JA. Tetrahedron Lett.  2002,  43:  1005 
    Google Scholar
  • 5i Molina P. Fresneda PM. García-Zafra S. Almendros P. Tetrahedron Lett.  1994,  35:  8851 
    Google Scholar
  • 6a Mali RS. Joshi PP. Sandhu PK. Manekar-Tilve A. J. Chem. Soc., Perkin Trans. 1  2002,  371 
    Google Scholar
  • 6b Mali RS. Pandhare NA. Sindkhedkar MD. Tetrahedron Lett.  1995,  36:  7109 
    Google Scholar
  • 6c Mali RS. Joshi PP. Sandhu PK. Manekar-Tive A. J. Chem. Soc., Chem. Commun.  1994,  251 
    Google Scholar
  • 6d Mali RS. Manekar AR. Tilve SG. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  1987,  26:  1 
    Google Scholar
  • 7a Kawasaki T. Shinada M. Kamimura D. Ohzono M. Ogawa A. Chem. Commun.  2006,  420 
    Google Scholar
  • 7b Quesada E. Taylor RJK. Synthesis  2005,  3193 
    Google Scholar
  • 7c Kawasaki T. Terashima R. Sakaguchi K. Sekiguchi H. Sakamoto M. Tetrahedron Lett.  1996,  37:  7525 
    Google Scholar
  • 8a Lin Y.-L. Kuo H.-S. Wang Y.-W. Huang S.-T. Tetrahedron  2003,  59:  1277 
    Google Scholar
  • 8b Zhang R.-Y. Zhao C.-G. Chem. Commun.  1996,  511 
    Google Scholar
  • 8c Kinder FR. Jarosinski MA. Anderson WK. J. Org. Chem.  1991,  56:  6475 
    Google Scholar
  • 8d Hatanaka M. Himeda Y. Ueda I. J. Chem Soc., Chem. Commun.  1990,  526 
    Google Scholar
  • 8e Baz ureau JP. Roux JL. Corre ML. Tetrahedron Lett.  1988,  29:  1921 
    Google Scholar
  • 8f Dartmann M. Flitsch W. Krebs B. Pandl K. Westfechtel A. Liebigs Ann. Chem.  1988,  695 
    Google Scholar
  • 8g Flitsch W. Wernsmann P. Tetrahedron Lett.  1981,  22:  719 
    Google Scholar
  • 9a Urbahns K. Kieck D. Göhrt A. Synthesis  1998,  1807 
    Google Scholar
  • 9b Yadav JS. Srinivas D. Tetrahedron Lett.  1997,  38:  7789 
    Google Scholar
  • 9c Wassermann HH. Shiraishi M. Coats SJ. Cook JD. Tetrahedron Lett.  1995,  36:  6785 
    Google Scholar
  • 9d Himeda Y. Hatanaka M. Ueda I. J. Chem Soc., Chem. Commun.  1995,  449 
    Google Scholar
  • 9e Himeda Y. Yamataka H. Ueda I. Hatanaka M. J. Org. Chem.  1997,  62:  6529 
    Google Scholar
  • 9f Burley I. Hewson T. Tetrahedron Lett.  1994,  35:  7099 
    Google Scholar
  • 10a Piva O. Comesse S. Eur. J. Org. Chem.  2000,  2417 
    Google Scholar
  • 10b McIntosh JM. Hayes IEE. Can. J. Chem.  1987,  65:  110 
    Google Scholar
  • 10c Minami T. Watanabe K. Hirakawa K. Chem. Lett.  1986,  2027 
    Google Scholar
  • 11a Breit B. Zahn SK. Tetrahedron  2005,  61:  6171 
    Google Scholar
  • 11b Breit B. Zahn SK. Angew. Chem., Int. Ed. Engl.  1999,  38:  969 
    Google Scholar
  • 12a Schobert R. Boeckmann RK. Pero JE. Org. Synth.  2005,  82:  140 
    Google Scholar
  • 12b Schobert R. Gordon GJ. Science of Synthesis: Houben-Weyl Methods of Molecular Transformations   Vol. 27:  Padwa A. Thieme; Stuttgart: 2004.  p.1047 
    Google Scholar
  • 12c Schobert R. Gordon GJ. Curr. Org. Chem.  2002,  6:  1181 
    Google Scholar
  • 12d Bestmann HJ. Schmidt M. Schobert R. Synthesis  1988,  49 
    Google Scholar
  • 12e Bestmann HJ. Sandmeier D. Angew. Chem., Int. Ed. Engl.  1975,  14:  634 
    Google Scholar
  • 13a Schobert R. Wicklein A. Synthesis  2007,  1499 
    Google Scholar
  • 13b Schobert R. Dietrich M. Mullen G. Urbina-Gonzales J.-M. Synthesis  2006,  3902 
    Google Scholar
  • 13c Schobert R. Jagusch C. J. Org. Chem.  2005,  70:  6129 
    Google Scholar
  • 13d Schobert R. Jagusch C. Synthesis  2005,  2421 
    Google Scholar
  • 13e Schobert R. Stangl A. Tetrahedron Lett.  2005,  46:  1127 
    Google Scholar
  • 13f Schobert R. Jagusch C. Melanophy C. Mullen G. Org. Biomol. Chem.  2004,  2:  3524 
    Google Scholar
  • 13g Schobert R. Jagusch C. Tetrahedron Lett.  2003,  44:  6449 
    Google Scholar
  • 13h Schobert R. Siegfried S. Nieuwenhuyzen M. Milius W. Hampel F. J. Chem. Soc., Perkin Trans. 1  2000,  1723 
    Google Scholar
  • 13i Löffler J. Schobert R. Liebigs Ann./Recl.  1997,  217 
    Google Scholar
  • 13j Löffler J. Schobert R. J. Chem. Soc., Perkin Trans. 1  1996,  2799 
    Google Scholar
  • 13k Bestmann HJ. Schmid D. Sandmeier D. Schade G. Oechsner H. Chem. Ber.  1985,  118:  1709 
    Google Scholar
  • 14a Saalfrank RW. Hafner W. Markmann J. Welch A. Peters K. von Schnering HG. Z. Naturforsch. B  1994,  49:  389 
    Google Scholar
  • 14b Saalfrank RW. Schierling P. Schaetzlein P. Chem. Ber.  1983,  116:  1463 
    Google Scholar
  • 14c Saalfrank RW. Schierling P. Hafner W. Chem. Ber.  1983,  116:  3482 
    Google Scholar
  • 14d Saalfrank RW. Ackermann E. Winkler H. Paul W. Boehme R. Chem. Ber.  1980,  113:  2950 
    Google Scholar
  • 14e Bestmann HJ. Saalfrank RW. Chem. Ber.  1976,  109:  403 
    Google Scholar
  • 15 Minami T. Motoyoshiya J. Synthesis  1992,  333 
    Article in Thieme ConnectGoogle Scholar
  • 16 Hatanaka M. Tanaka Y. Himeda Y. Ueda I. Tetrahedron Lett.  1993,  34:  4837 
    CrossrefGoogle Scholar
  • 17 Reichardt C. Solvents and Solvent Effects in Organic Chemistry   2nd ed.:  VCH; Weinheim: 1988. 
    Google Scholar
  • 18 Pietrusiewicz KM. Monkiewicz J. Tetrahedron Lett.  1986,  27:  739 
    CrossrefGoogle Scholar
  • 19 Sharma GVM. Rajendra Prasad T. Radha Krishna P. Krishnudu K. Ramana Rao MHV. Kunwar AC. J. Carbohydr. Chem.  2002,  21:  501 
    Google Scholar
  • 20 Guiney D. Gibson CL. Suckling CJ. Org. Biomol. Chem.  2002,  664 
    Google Scholar
  • 21 Corey EJ. Kamiyama K. Tetrahedron Lett.  1990,  31:  3995 
    CrossrefGoogle Scholar
  • 22 Jamie JF. Rickards RW. J. Chem. Soc., Perkin Trans. 1  1997,  3613 
    CrossrefGoogle Scholar
  • 23 Moorhoff CM. Schneider DF. Tetrahedron Lett.  1987,  28:  4721 
    CrossrefGoogle Scholar
  • 24 Moorhoff CM. J. Chem. Soc., Perkin Trans. 1  1997,  1987 
    CrossrefGoogle Scholar
  • 25 Muxfeldt H. Grethe G. Uhlig K. Zeugner H. Chem. Ber.  1963,  96:  2943 
    CrossrefGoogle Scholar
  • 26 Serratosa F. Sole E. An. R. Soc. Esp. Fis. Quim., Ser.  1966,  62:  431 ; Chem. Abstr. 1967, 66, 2623f
    Google Scholar
  • 27 Kato N. Katagiri N. Takashima K. J. Chem. Soc., Chem. Commun.  1982,  664 
    CrossrefGoogle Scholar
  • 28 Pietrusiewicz KM. Monkiewicz J. J. Org. Chem.  1983,  48:  788 
    CrossrefGoogle Scholar
  • 29 Bodalski R. Pietrusiewicz KM. Monkiewicz J. Koszuk J. Tetrahedron Lett.  1980,  21:  2287 
    CrossrefGoogle Scholar
  • 30 Davis M. Wu W.-Y. Aust. J. Chem.  1988,  41:  1591 
    CrossrefGoogle Scholar
  • 31 Sun KM. Dawe RD. Fraser-Reid B. Carbohydr. Res.  1987,  171:  35 
    CrossrefGoogle Scholar
  • 32 Holtz E. Albrecht U. Langer P. Tetrahedron  2007,  63:  3293 
    CrossrefGoogle Scholar
  • 33 Lopez Herrera FJ. Uraga Baelo C. Carbohydr. Res.  1985,  139:  95 
    Google Scholar
  • 34 Hatanaka M. Tanaka Y. Ueda I. Tetrahedron Lett.  1995,  36:  3719 
    CrossrefGoogle Scholar
  • 35 Hatanaka M. Ishida A. Tanaka Y. Himeda Y. Ueda I. Tetrahedron Lett.  1996,  37:  401 
    CrossrefGoogle Scholar
  • 36 Karagiri N. Takashima K. Haneda T. Kato T. J. Chem. Soc., Perkin Trans. 1  1984,  553 
    CrossrefGoogle Scholar
  • 37 Zbiral E. Oehler E. Chem. Ber.  1980,  113:  2852 
    Google Scholar
  • 38 Moorhoff CM. Monatsh. Chem.  2003,  134:  429 
    CrossrefGoogle Scholar
  • 39 Sancaktar EA. Taylor JD. Hay JV. Wolfe JF. J. Org. Chem.  1976,  41:  509 
    Google Scholar
  • 40a Langer P. Kracke B. Synlett  2001,  1790 
    Google Scholar
  • 40b Pietrusiewicz KM. Salamoñczyk I. J. Org. Chem.  1988,  53:  2837 
    Google Scholar
  • 40c Gurjar MK. Rama Devi T. Reddy KL. Sharma PA. Murali Dhar TG. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  1993,  32:  995 
    Google Scholar
  • 40d Sharma GVM. Subhash Chander A. Radha Krishna P. Krishnudu K. Ramana Rao MHV. Kunwar AC. Tetrahedron: Asymmetry  2000,  11:  2643 
    Google Scholar
  • 41 Sharma GVM. Rajendra Prasad T. Radha Krishna P. Krishnudu K. Ramana Rao MHV. Kunwar AC. Tetrahedron: Asymmetry  2000,  11:  4499 
    CrossrefGoogle Scholar
  • 42 For a detailed discussion on the analogous NaH-RONa complex, see: Caubère P. Top. Curr. Chem.  1978,  73:  105 
    Google Scholar
  • 43 Moorhoff CM. Schneider DF. Winkler D. J. Chem. Res., Miniprint  1998,  3461 
    Google Scholar
  • 44 Bankwell MG. Cameron JM. Tetrahedron Lett.  1996,  37:  525 
    CrossrefGoogle Scholar
  • 45 Polonsky J. Varon Z. Jacquemin H. Donnelly DMX. Meegan MJ. J. Chem. Soc., Perkin Trans. 1  1980,  2065 
    CrossrefGoogle Scholar
  • 46 Tanenbaum SW. Agarwal SC. Williams T. Pitcher RG. Tetrahedron Lett.  1970,  2377 
    CrossrefGoogle Scholar
  • 47a Nishikawa H. Nippon Nogei Kagaku Kaishi  1933,  9:  772 
    Google Scholar
  • 47b Sasaki M. Kaneko Y. Oshita K. Takamatsu H. Yokotsuka T. Agric. Biol. Chem.  1970,  34:  1296 
    Google Scholar
  • 47c Grove JF. Pople M. J. Chem. Soc., Perkin Trans. 1  1979,  2048 
    Google Scholar
  • 48 Stodola FH. Cabot C. Benjamin C. Biochem. J.  1964,  93:  92 
    CrossrefGoogle Scholar
  • 49 Moorhoff CM. J. Chin. Chem. Soc.  2003,  50:  419 
    CrossrefGoogle Scholar
  • 50 Miyamoto M. Kanamatsu Y. Kawashima K. Shimohasa M. Tanaka K. Tatsuoka S. Nakanishi K. Tetrahedron  1967,  23:  421 
    CrossrefGoogle Scholar
  • 51 Bakhaeva GP. Berlin AY. Boldyreva E. Chuprunova OA. Kolosov MN. Soifer VS. Vasiljeva TE. Yartseva IV. Tetrahedron Lett.  1968,  32:  3595 
    Google Scholar
  • 52 Berlin AY. Kieseleva OA. Shemyakin MN. Soifer VS. Yartseva IV. Kuznetsov YD. Nature  1968,  218:  193 
    CrossrefGoogle Scholar
  • 53 Kimura Y. Mizuno T. Shimada A. Tetrahedron Lett.  1996,  37:  469 
    Google Scholar
  • 54 Kraus GA. Zheng D. Synlett  1993,  71 
    Article in Thieme ConnectGoogle Scholar
  • 55 For a review on the chemistry and biology of Taxol, see: Nicolaou KC. Dai W.-M. Guy RK. Angew. Chem., Int. Ed. Engl.  1994,  33:  15 
    CrossrefGoogle Scholar
  • 56 Hegde SG. Bryant RD. Synth. Commun.  1993,  23:  2753 
    CrossrefGoogle Scholar
  • 57 Clerici F. Folpini E. Gelmi ML. Pocar D. Tetrahedron  1991,  47:  8907 
    CrossrefGoogle Scholar
  • 58 Römpp Lexikon Naturstoffe   Steglich W. Fugmann B. Lang-Fugmann S. Thieme; Stuttgart: 1997. 
    Google Scholar
  • 59 Pettit GR. Toki B. Herald DL. Verdier-Pinard P. Boyd MR. Hamel E. Pettit RK. J. Med. Chem.  1998,  41:  1688 
    CrossrefGoogle Scholar
  • 60 Liou J.-P. Chang J.-Y. Chang C.-W. Chang C.-Y. Mahindroo N. Kuo F.-M. Hsieh H.-P. J. Med. Chem.  2004,  47:  2897 
    CrossrefGoogle Scholar
  • 61 Liou J.-P. Chang C.-W. Song JS. Yang YS. Yeh CF. Tseng HY. Lo YK. Chang C.-L. Chang CM. Hsieh H.-P. J. Med. Chem.  2002,  45:  2556 
    CrossrefGoogle Scholar
  • 62 Holtz E. Langer P. Synlett  2003,  402 
    Article in Thieme ConnectGoogle Scholar
  • 63 Albrecht U. Nguyen THV. Langer P. J. Org. Chem.  2004,  69:  3417 
    CrossrefGoogle Scholar
  • 64a Gill M. Steglich W. Prog. Chem. Org. Nat. Prod.  1987,  51:  1 
    Google Scholar
  • 64b Shi Q. Verdier-Pinard P. Brossi A. Hamel E. McPhail AT. Lee K.-H. J. Med. Chem.  1997,  40:  961 
    Google Scholar
  • 64c Shi Q. Chen K. Brossi A. Verdier-Pinard P. Hamel E. McPhail AT. Lee K.-H. Helv. Chim. Acta  1998,  81:  1023 
    Google Scholar
  • 64d Dürckheimer W. Paulus EF. Angew. Chem., Int. Ed. Engl.  1985,  24:  224 ; Angew. Chem. 1985, 97, 219
    Google Scholar
  • 64e Klostermeyer D. Knops L. Sindlinger T. Polborn K. Steglich W. Eur. J. Org. Chem.  2000,  603 
    Google Scholar
  • 65a Friedrichsen W. In Comprehensive Heterocyclic Chemistry   Vol. 2:  Katritzky AR. Rees CW. Scriven EFV. Elsevier; Amsterdam: 1996.  p.359 ; and references cited therein
    Google Scholar
  • 65b König B. In Science of Synthesis   Vol. 9:  Maas G. Thieme; Stuttgart: 2000.  p.183 
    Google Scholar
  • 65c Marshall JA. Sehon CA. J. Org. Chem.  1995,  60:  5966 
    Google Scholar
  • 65d Sperry JB. Whitehead CR. Ghiviriga I. Walczak RM. Wright DL. J. Org. Chem.  2004,  69:  3726 
    Google Scholar
  • 65e Shun ALKS. Tykwinski RR. J. Org. Chem.  2003,  68:  6810 
    Google Scholar
  • 66 Mross G. Holtz E. Langer P. J. Org. Chem.  2006,  71:  8045 
    CrossrefGoogle Scholar
  • 67 Holtz E. Langer P. Synlett  2004,  1805 
    Article in Thieme ConnectGoogle Scholar
  • 68a D’Ambrosio M. Guerriero A. Pietra F. Helv. Chim. Acta  1987,  70:  2019 
    Google Scholar
  • 68b D’Ambrosio M. Guerriero A. Pietra F. Helv. Chim. Acta  1988,  71:  964 
    Google Scholar
  • 68c Ciomei M. Albanese C. Pastori W. Grandi M. Pietra F. D’Ambrosio M. Guerriero A. Battistini C. Proc. Am. Assoc. Cancer Res.  1997,  38:  Abstract 30 
    Google Scholar
  • 68d Battistini C, Ciomei M, Pietra F, D’Ambrosio M, and Guerriero A. inventors; PCT Int. Appl. WO  36335.  (Pharmacia S.p.A.)
  • 69a Lindel T. Jensen PR. Fenical W. Long BH. Casazza AM. Carboni J. Fairchild CR. J. Am. Chem. Soc.  1997,  119:  8744 
    Google Scholar
  • 69b Fenical W, Jensen PR, and Lindel T. inventors; US Patent  A5473057.  (University of California) ; Chem. Abstr. 1996, 124, P194297z
  • 70 Nicolaou KC. Kim S. Pfefferkorn J. Xu J. Ohshima T. Hosokawa S. Vourloumis D. Li T. Angew. Chem., Int. Ed. Engl.  1998,  37:  1418 
    CrossrefGoogle Scholar
  • 71a Ceccarelli SM. Piarulli U. Gennari C. Tetrahedron  2001,  57:  8531 
    Google Scholar
  • 71b Ceccarelli S. Piarulli U. Gennari C. Tetrahedron Lett.  1999,  40:  153 
    Google Scholar
  • 72 Gelmi ML. Pocar D. Synthesis  1992,  453 
    Article in Thieme ConnectGoogle Scholar
  • 73 Hatanaka M. Imashiro R. Ueda I. Chem. Lett.  1992,  2253 
    CrossrefGoogle Scholar
  • 74 Hatanaka M. Himeda Y. Imashiro R. Tanaka Y. Ueda I. J. Org. Chem.  1994,  59:  111 
    CrossrefGoogle Scholar
  • 75 Cao W. Ding W. Yi T. Zhu Z. J. Fluorine Chem.  1997,  81:  153 
    CrossrefGoogle Scholar
  • 76 Yang Z. Shannon D. Truong V.-L. Deslongchamps P. Org. Lett.  2002,  4:  4693 
    CrossrefGoogle Scholar
  • 77 Kawano T. Negoro K. Ueda I. Tetrahedron Lett.  1997,  47:  8219 
    Google Scholar
  • 78 Chapdelaine D. Dube P. Deslongchamps P. Synlett   2000,  1819 
    Google Scholar
  • 79 Tanaka Y. Kawano T. Islam S. Nishioka H. Hatanaka M. Ueda I. Chem. Pharm. Bull.  1996,  44:  885 
    CrossrefGoogle Scholar
  • 80 Bestmann H.-J. Roth K. Angew. Chem., Int. Ed. Engl.  1981,  20:  575 
    CrossrefGoogle Scholar
  • 81 Bestmann H.-J. Saalfrank RW. Chem. Ber.  1976,  109:  403 
    CrossrefGoogle Scholar
  • 82 Moorhoff CM. Monatsh. Chem.  2003,  134:  61 
    Google Scholar
  • 83 Himeda Y. Hiratani K. Hatanaka M. Ueda I. J. Chem. Soc., Chem. Commun.  1992,  1684 
    CrossrefGoogle Scholar
  • 84 Hatanaka M. Himeda Y. Ueda I. Tetrahedron Lett.  1991,  35:  4521 
    Google Scholar
  • 85 Schoop A. Greiving H. Göhrt A. Tetrahedron Lett.  2000,  41:  1913 
    CrossrefGoogle Scholar
  • 86a King ML. Chiang CC. Ling HC. Fujita E. Ochiai M. McPhail AT. J. Chem. Soc., Chem. Commun.  1982,  1150 
    Google Scholar
  • 86b Satasook C. Isman MB. Wiriyachitra P. Pestic. Sci.  1992,  36:  53 
    Google Scholar
  • 86c Janprasert J. Satasook C. Sukumalanand P. Champagne DE. Isman MB. Wiriyachitra P. Towers GH. Phytochemistry  1993,  32:  67 
    Google Scholar
  • 86d Nugroho BW. Edrada RA. Güssregen B. Wray V. Witte L. Proksch P. Phytochemistry  1997,  44:  1455 
    Google Scholar
  • 87 Takayasu T. Nitta M. J. Chem. Soc., Perkin Trans. 1  1997,  681 
    CrossrefGoogle Scholar
  • 88 Takayasu T. Nitta M. J. Chem. Soc., Perkin Trans. 1  1997,  3255 
    CrossrefGoogle Scholar
  • 89 Himeda Y. Tanaka Y. Ueda I. Hatanaka M. J. Chem. Soc., Perkin Trans. 1  1998,  1389 
    CrossrefGoogle Scholar
  • 90 Hatanaka M. Himeda Y. Tanaka Y. Ueda I. Tetrahedron Lett.  1995,  36:  3211 
    CrossrefGoogle Scholar
  • 91 Kitano H. Fujita S. Takehara Y. Hattori M. Morita T. Matsumoto K. Hatanaka M. Tetrahedron  2003,  59:  2673 
    CrossrefGoogle Scholar