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Synlett 2014; 25(6): 799-804
DOI: 10.1055/s-0033-1340794
DOI: 10.1055/s-0033-1340794
letter
Synthesis of Functionalized Octahydroindoles Related to Daphnyphyllum Alkaloids
Further Information
Publication History
Received: 16 December 2013
Accepted after revision: 16 January 2014
Publication Date:
24 February 2014 (online)
Abstract
Functionalized octahydroindoles were synthesized from (±)-cyclohex-2-en-1-ol as potential intermediates for convergent syntheses of several alkaloids from plants of the Daphnyphyllum genus.
Key words
alkaloids - heterocycles - bicyclic compounds - natural products - hydrogenation - diastereoselectivitySupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
References and Notes
- 1 Kobayashi J, Kubota T. Nat. Prod. Rep. 2009; 26: 936 ; and references cited therein
- 2 Vincent M, Marchand B, Remond G, Jaguelin-Guinamant S, Damien G, Portevin B, Baumal JY, Volland JP. Drug Des. Discovery 1992; 9: 11
- 3 Niwa H, Hirata Y, Suzuki KT, Yamamura S. Tetrahedron Lett. 1973; 14: 2129
- 4a Coldham I, Burrell AJ. M, Guerrand HD. S, Oram N. Org. Lett. 2011; 13: 1267
- 4b Bélanger G, Boudreault J, Lévesque F. Org. Lett. 2011; 13: 6204
- 4c Denmark SE, Baiazitov RY. J. Org. Chem. 2006; 71: 593
- 4d Solé D, Urbaneja X, Bonjoch J. Org. Lett. 2005; 7: 5461
- 5 Hanessian S, Dorich S, Menz H. Org. Lett. 2013; 15: 4134
- 6 Hanessian S, Dorich S, Kassem S, Menz H, Chattopadhyay A. Tetrahedron 2014; 70: 439
-
7 For the preparation of enantiomerically pure cyclohex-2-en-1-ol, see: Holub N, Neidhofer J, Blechert S. Org. Lett. 2005; 7: 1227
- 8 Elhalem E, Comin MJ, Rodriguez JB. Eur. J. Org. Chem. 2006; 4473
- 9a Murata S, Suzuki M, Noyori R. J. Am. Chem. Soc. 1979; 101: 2738
- 9b Mehta G, Umarye JD, Gagliardini V. Tetrahedron Lett. 2002; 43: 6975
- 9c Burke SD, Letourneau JJ, Matulenko MA. Tetrahedron Lett. 1999; 40: 9
- 10 Mitsunobu O, Yamada Y. Bull. Chem. Soc. Jpn. 1967; 40: 2380
- 11a Uesaka N, Saitoh F, Mori M, Shibasaki M, Okamura K, Dates K. J. Org. Chem. 1994; 59: 5633
- 11b Negishi E, Cederbaum FE, Takahashi T. Tetrahedron Lett. 1986; 27: 2829
- 12 Hayashi N, Shibata I, Baba A. Org. Lett. 2004; 6: 4981
- 13a Trost BM, Toste FD. Tetrahedron Lett. 1999; 40: 7739
- 13b Trost BM, Machacek M, Schnaderneck MJ. Org. Lett. 2000; 2: 1761
- 13c Trost BM, Ashfeld BL. Org. Lett. 2008; 10: 1893
- 14a Yamada H, Aoyagi S, Kibayashi C. Tetrahedron Lett. 1996; 37: 8787
-
14b Trost BM, Tanoury GJ, Lautens M, Chan C, MacPherson DT. J. Am. Chem. Soc. 1994; 116: 4255
- 15a Stork G, Mook R. J. Am. Chem. Soc. 1987; 109: 2829
- 15b Clive DL. J, Coltart DM. Tetrahedron Lett. 1998; 39: 2519
- 15c Shanmugam P, Srinivasan R, Rajagopalan K. Tetrahedron 1997; 53: 11685
- 15d Clive DL. J, Coltart DM, Zhou Y. J. Org. Chem. 1999; 64: 1447
- 15e Clive DL. J, Magnuson SR, Manning HW, Mayhew DL. J. Org. Chem. 1996; 61: 2095
- 15f Alcaide B, Rodríguez-Campos IM, Rodríguez-López J, Rodríguez-Vicente A. J. Org. Chem. 2004; 64: 5377
- 15g Ko HM, Lee CW, Kwon HK, Chung HS, Choi SY, Chung YK, Lee E. Angew. Chem. Int. Ed. 2009; 48: 2364
- 16 See the Supporting Information.
- 17 Marsh BJ, Carbery DR. J. Org. Chem. 2009; 74: 3186
- 18a Birch AJ. J. Chem. Soc. 1944; 430
- 18b Birch AJ. J. Chem. Soc. 1945; 809
- 18c Birch AJ. J. Chem. Soc. 1946; 593
- 19 Wilds AL, Nelson NA. J. Am. Chem. Soc. 1953; 75: 5360
- 20 When the elaboration of bicyclic intermediates was carried out with diastereoisomers 10 and 11 separately, they were found to show similar reactivities and yields to one another.
- 21 Crabtree SR, Chu WL. A, Mander LN. Synlett 1990; 169
- 22 Lazny R, Nodzewska A. Chem. Rev. 2010; 110: 1386
- 23a Nicolaou KC, Montagnon T, Baran PS, Zhong Y.-L. J. Am. Chem. Soc. 2002; 124: 2245
- 23b Duschek A, Kirsch SF. Angew. Chem. Int. Ed. 2011; 50: 1524
- 24a Reich HJ, Wollowitz S. Org. React. (N. Y.) 1993; 44: 1
- 24b Ghosh AK, Xi K. J. Org. Chem. 2009; 74: 1163
- 24c Bartona DR, Brewsterra AG, Hui RA. H. F, Lester JD, Ley SV. J. Chem. Soc., Chem. Commun. 1978; 952
- 24d Dragojlovic V. J. Chem. Res., Synop. 1999; 256
- 24e Holl R, Schepmann D, Fröhlich R, Grünert R, Bednarski PJ, Wünsch B. J. Med. Chem. 2009; 52: 2126
- 24f Liotta D, Monahan R. Science 1986; 231: 356
- 25a Lian J.-J, Chen P.-C, Lin Y.-P, Ting H.-C, Liu R.-S. Chem. Commun. 2007; 1337
- 25b Knobloch K, Keller M, Eberbach W. Eur. J. Org. Chem. 2001; 3313
- 25c Utsugi M, Miyano M, Nakada M. Org. Lett. 2006; 8: 2973
- 25d LaFrate AL, Gunther JR, Carlson KE, Katzenellenbogen JA. Bioorg. Med. Chem. 2008; 16: 10075
- 26a Bredereck H, Simchen G, Rebsdat S, Kantlehner W, Horn P, Wahl R, Hoffmann H, Grieshaber P. Chem. Ber. 1968; 101: 41
- 26b Rosso GB. Synlett 2006; 809
- 26c Fontenas C, Aït-Haddou H, Bejan E, Balavoine GG. A. Synth. Commun. 1998; 28: 1743
- 26d Shawe TT, Hansen DB, Peet KA, Prokopowicz AS, Robinson PM, Cannon A, Dougherty KE, Ross AA, Landino LM. Tetrahedron 1997; 53: 1547
- 26e Andrew RJ, Mellor JM. Tetrahedron 2000; 56: 7261
- 27 Krief A, Dumont W, Kremer A. Tetrahedron Lett. 2009; 50: 2398
- 28 We observed that, among other factors, the rate of addition of Br2 affected the yield; optimal yields of 26 were obtained when Br2 was added rapidly under vigorous stirring.
- 29a Openshaw HT, Robinson R. J. Chem. Soc. 1946; 912
- 29b Sevenard DV, Kazakova O, Schoth R.-M, Lork E, Chizhov DL, Poveleit J, Röschenthaler G.-V. Synthesis 2008; 1867
- 29c Shukla R, Rathore R. Synthesis 2008; 3769
- 29d Rathore R, Kochi JK. J. Org. Chem. 1995; 60: 4399
- 30a Sünnemann HW, Banwell MG, De Meijere A. Eur. J. Org. Chem. 2007; 3879
- 30b Sünnemann HW, De Meijere A. Angew. Chem. 2004; 43: 895
- 30c Von Zezschwitz P, Petry F, De Meijere A. Chem. Eur. J. 2001; 7: 4035
- 30d Masters K.-S, Flynn BL. Adv. Synth. Catal. 2009; 351: 530
- 30e Hayashi R, Fernandez S, Okamura WH. Org. Lett. 2002; 4: 851
- 30f Ilaldinov IZ, Bukharov SV, Kadyrov R. Russ. J. Org. Chem. (Engl. Transl.) 2007; 43: 747
- 31 With THF, Et2O, toluene, or THF–HMPA (10:1) as solvent. All the above reactions were also tried with addition of the base to the premixed bromo ketone and electrophile. Also, extended reaction times (2‒3 d) were tried, but produced no improvement.
- 32 The chloro ketone analogous to 26 was also formed but gave the same unexpected results during attempts to form the corresponding chloro enol triflate.
- 33 Gavrin LK, Lee A, Provencher BA, Massefski WW, Huhn SD, Ciszewski GM, Cole DC, McKew JC. J. Org. Chem. 2007; 72: 1043
- 34a Numazawa M, Satoh M, Satoh S, Nagaoka M. J. Org. Chem. 1986; 51: 1360
- 34b Wong S.-C, Sasso S, Jones H, Kaminski JJ. J. Med. Chem. 1984; 27: 20
- 35 Crystallographic data for compounds 9, 11, 17, 27, 28, and 32 have been deposited with the accession numbers CCDC 968290, 968291, 968292, 968293, 968294, and 968295, respectively, and can be obtained free of charge from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk; Web site: www.ccdc.cam.ac.uk/conts/retrieving.html.
For selected examples of synthetic approaches to related alkaloids, see:
For examples of the use of this strategy, see: