A Highly Effective Diels-Alder Approach to cis-Clerodane Natural Products: First Total Synthesis of Solidago Alcohol

Tai Wei Ly; Jyh-Hsiung Liao; Kak-Shan Shia; Hsing-Jang Liu

doi:10.1055/s-2004-815916

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2004(2): 271-275
DOI: 10.1055/s-2004-815916

PAPER

A Highly Effective Diels-Alder Approach to cis-Clerodane Natural Products: First Total Synthesis of Solidago Alcohol

Tai Wei Ly^a,1, Jyh-Hsiung Liao^a,b, Kak-Shan Shia^b, Hsing-Jang Liu*^a,b
^a Institute of Chemistry, Academia Sinica, Nankang, Taipei, 11592 Taiwan, Republic of China
^b Department of Chemistry, National Tsing Hua University, Hsinchu, 30043 Taiwan, Republic of China
e-Mail: hjliu@mx.nthu.edu.tw;

Further Information

Publication History

Received 2 October 2003
Publication Date:
13 January 2004 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

The first total synthesis of solidago alcohol (8) has been achieved in racemic form. The synthetic endeavor takes advantage of a facile and highly face-selective Diels-Alder cycloaddition reaction of cross-conjugated β-keto ester 3, readily accessible from 3-ethoxy-2-cyclohexenone, and trans-piperylene.

Key words

Diels-Alder reaction - diterpene - total synthesis - natural product - diastereoselectivity

References

2a Merritt AT. Ley SV. Nat. Prod. Rep. 1992, 9: 243

Crossref Google Scholar
2b Tokoroyama T. J. Synth. Org. Chem. Jpn. 1993, 51: 1164

Crossref Google Scholar
3a Nakanishi K. Insect Biology of the Future Locke M. Smith DS. Academic Press; New York: 1980.

Google Scholar
3b Philogene BJR. Ann. de la Société Entomologique du Québec 1974, 19: 121

Google Scholar
4 Manabe S. Nishino C. Tetrahedron 1986, 42: 3461

Crossref Google Scholar
5 Valdes LJ. Butler WM. Hatfield GM. Paul AG. Koreeda M. J. Org. Chem. 1984, 49: 4716

Crossref Google Scholar
6 Andersen NR. Rasmussen PR. Falshaw CP. King TJ. Tetrahedron Lett. 1984, 25: 469

Crossref Google Scholar
7 Wagner H. Seitz R. Lotter H. Herz W. J. Org. Chem. 1978, 48: 3339

Google Scholar
8a Tamamura T. Sawa T. Isshiki K. Masuda T. Homma Y. Iinuma H. Naganawa H. Hamada M. Takeuchi T. Umezawa H. J. Antibiot. 1985, 38: 1664

Crossref Google Scholar
8b Isshiki K. Tamamura T. Takahashi Y. Sawa T. Naganawa H. Takeuchi T. Umezawa H. J. Antibiot. 1985, 38: 1819

Crossref Google Scholar
9 Rojas-Garciduenas M. Dominguez XA. Turrialba 1976, 26: 10

Google Scholar
10a Tsuji H. Tani Y. Ueda H. Nippon Kagaku Kaishi 1977, 51: 609

Google Scholar
10b Tsuji H. Tani Y. Ueda H. Bokin Bobai 1978, 6: 170

Google Scholar
11 Kitazawa E. Sato A. Takahashi S. KuKuwano H. Ogiso A. Chem. Pharm. Bull. 1980, 28: 227

Crossref Google Scholar
For the trans series:
12a Tokoroyama T. Matsuo K. Kubota T. Tetrahedron 1978, 34: 1907

Crossref Google Scholar
12b Takahashi S. Kusumi T. Kakisawa H. Chem. Lett. 1979, 515

Crossref Google Scholar
12c Tokoroyama T. Matsuo K. Kotsuki H. Kanazawa R. Tetrahedron 1980, 36: 3377

Crossref Google Scholar
12d Luteijn HM. de Groot AE. Tetrahedron Lett. 1982, 3: 3421

Crossref Google Scholar
12e Kende AS. Roth B. Kubo I. Tetrahedron Lett. 1982, 23: 1751

Crossref Google Scholar
12f Sharma AS. Chattopadhyay P. J. Org. Chem. 1982, 47: 1727

Crossref Google Scholar
12g Ley SV. Simpkins NS. Whittle AJ. J. Chem. Soc., Chem. Commun. 1983, 503

Crossref Google Scholar
12h Sharma AS. Gayen AK. Tetrahedron 1985, 41: 4581

Crossref Google Scholar
12i Jones PS. Ley SV. Simpkins NS. Whittle AJ. Tetrahedron 1986, 42: 6519

Crossref Google Scholar
12j Iio H. Monden M. Okada K. Tokoroyama T. J. Chem. Soc., Chem. Commun. 1987, 358

Crossref Google Scholar
12k Piers E. Wai JSM. J. Chem. Soc., Chem. Commun. 1987, 1342

Crossref Google Scholar
12l Piers E. Wai JSM. J. Chem. Soc., Chem. Commun. 1988, 1245

Crossref Google Scholar
12m Piers E. Fleming FF. J. Chem. Soc., Chem. Commun. 1989, 1665

Crossref Google Scholar
12n Hagiwara H. Inome K. Uda H. Tetrahedron Lett. 1994, 35: 8189

Crossref Google Scholar
12o Piers E. Wai JSM. Can. J. Chem. 1994, 72: 146

Crossref Google Scholar
12p Bruner SD. Radeke HS. Tallarico JA. Snapper ML. J. Org. Chem. 1995, 60: 1114

Crossref Google Scholar
12q Hagiwara H. Inome K. Uda H. J. Chem. Soc., Perkin Trans. 1 1995, 757

Crossref Google Scholar
12r Goldsmith DJ. Deshpande R. Synlett 1995, 495

Crossref Google Scholar
12s Kato M. Kosugi H. Ichiyanagi T. Suzuki T. Tetrahedron Lett. 1999, 40: 5377

Crossref Google Scholar
12t Paquette LA. Efremov I. J. Am. Chem. Soc. 2000, 122: 9324

Crossref Google Scholar
12u Olkhovik V. Masalov N. Jansen BJM. de Groot A. Tetrahedron Lett. 2001, 42: 4903

Crossref Google Scholar
12v Grossman RB. Rasne RM. Org. Lett. 2001, 3: 4027

Crossref Google Scholar
For the cis series:
13a Tokoroyama T. Fujimori K. Shimizu T. Yamagiwa Y. Monden M. Iio H. J. Chem. Soc., Chem. Commun. 1983, 1516

Article in Thieme Connect Google Scholar
13b Tokoroyama T. Tsukamoto M. Asada T. Iio H. Tetrahedron Lett. 1987, 28: 6645

Article in Thieme Connect Google Scholar
13c Tokoroyama T. Fujimori K. Shimizu T. Yamagiwa Y. Monden M. Iio H. Tetrahedron 1988, 44: 6607

Article in Thieme Connect Google Scholar
13d Tokoroyama T. Kanazawa R. Yamamoto S. Kamikawa T. Suenaga H. Miyabe M. Bull. Chem. Soc. Jpn. 1990, 63: 1720

Article in Thieme Connect Google Scholar
13e Piers E. Breau ML. Han Y. Plourde GL. Yeh WL. J. Chem. Soc., Perkin Trans. 1 1995, 963

Article in Thieme Connect Google Scholar
13f Liao CC. Lee TH. Tetrahedron Lett. 1996, 6869

Article in Thieme Connect Google Scholar
13g Liao CC. Liu WC. Synlett 1998, 912

Article in Thieme Connect Google Scholar
13h Wu JD. Shia KS. Liu HJ. Tetrahedron Lett. 2001, 42: 4207

Article in Thieme Connect Google Scholar
13i Liu HJ. Ho YL. Wu JD. Shia KS. Synlett 2001, 1805

Article in Thieme Connect Google Scholar
13j Suzuki A. Nakatani M. Nakamura M. Kawaguchi K. Inoue M. Katoh T. Synlett 2003, 329

Article in Thieme Connect Google Scholar
13k For the 19-nor series: Liu HJ. Zhu JL. Chen IC. Jankowska R. Han Y. Shia KS. Angew. Chem. Int. Ed. 2003, 42: 1851

Article in Thieme Connect Google Scholar
13l For recent reviews on various synthetic approaches: Tokoroyama T. Synthesis 2000, 611

Article in Thieme Connect Google Scholar
13m Also see: Ly TW. Shia KS. Liu HJ. Latest Frontiers of Organic Synthesis Kobayashi Y. Research Signpost; India: 2002.

Article in Thieme Connect Google Scholar
14 Liu HJ. Shia KS. Han Y. Sun D. Wang Y. Can. J. Chem. 1997, 75: 646

Crossref Google Scholar
15 Liu HJ. Shia KS. Tetrahedron 1998, 54: 13449

Crossref Google Scholar
16 Liu HJ. Shia KS. Han Y. Wang Y. Synlett 1995, 545

Article in Thieme Connect Google Scholar
17a Anthonsen T. Henderson MS. Martin A. McCrindle R. Murray RDH. Acta. Chem. Scand. 1968, 22: 351

Crossref Google Scholar
17b Henderson MS. McCrindle R. McMaster D. Can. J. Chem. 1973, 51: 1346

Crossref Google Scholar
18a Mandal AK. Soni NR. Ratnam KR. Synthesis 1985, 275

Google Scholar
18b Vankar YD. Rao CT. J. Chem. Res., Synop. 1985, 232

Google Scholar
19 Bhatt MV. Kulkarni SU. Synthesis 1983, 249

Article in Thieme Connect Google Scholar
20a Schmidt AH. Aldrichimica Acta 1981, 14: 31

Crossref Google Scholar
20b Olah GA. Narang SC. Gupta BGB. Malhotra R. J. Org. Chem. 1979, 44: 1247

Crossref Google Scholar
20c Jung ME. Lyster MA. J. Org. Chem. 1977, 42: 3761

Crossref Google Scholar
21a Boekman RK. Potenza JC. Tetrahedron Lett. 1985, 26: 1411

Crossref Google Scholar
21b King PF. Stroud SG. Tetrahedron Lett. 1985, 26: 1415

Crossref Google Scholar
22a Kornblum N. Jones WJ. Anderson GJ. J. Am. Chem. Soc. 1959, 81: 4113

Crossref Google Scholar
22b Johnson AP. Pelter A. J. Chem. Soc. 1964, 520

Crossref Google Scholar
22c Ganem B. Boeckman RK. Tetrahedron Lett. 1974, 917

Crossref Google Scholar
23 Still WC. Kahn M. Mitra A. J. Org. Chem. 1978, 43: 2923

Crossref Google Scholar
24 Perrin DD. Armarego WLF. Perrin DR. Purification of Laboratory Chemicals Pergamon Press; Oxford: 1987.

Google Scholar

1

Current address: Department of Chemistry, Research Center Kyoto, Bayer Yakuhin Ltd., 6-5-1-3, Kunimidai, Kizu-cho, Soraku-gun, Kyoto 619-0216, Japan.