Total synthesis of (±)-scirpene

Organic Letters

Volumn 1, Issue 3, 1999, Pages 517-519

  Nemoto, Hideo ^a,b   Takahashi, Eiki ^a   Ihara, Masataka ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000675932     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9901164     Document Type: Article

References (15)

1. (a) Kupchan, S. M.; Jarvis, B. B.; Dailey, R. G., Jr.; Bright, W.; Bryan, R. F.; Shizuri, Y. J. Am. Chem. Soc. 1976, 98, 7092-7093.
2. (b) Ueno, Y. Trichothecenes - Chemical, Biological and Toxicological Aspects, Developments in Food Science 4; American Elsevier: New York, 1983.
3. Iida, A.; Konishi, K.; Kubo, H.; Tomioka, K.; Tokuda, H.; Nishino, H. Tetrahedron Lett. 1996, 37, 9219-9220.
4. Ishihara, J.; Nonaka, R.; Terasawa, Y.; Shiraki, R.; Yabu, K.; Kataoka, H.; Ochiai, Y.; Tadano, K. J. Org. Chem. 1998, 63, 2678-2688 and references therein.
5. Nemoto, H.; Fukumoto, K. Synlett 1997, 863-875.
6. Nemoto, H.; Miyata, J.; Ihara, M. Tetrahedron Lett. 1999, 40, 1933-1936.
7. Isolation: Machida, Y.; Nozoe, S. Tetrahedron 1972, 28, 5113-5117.
8. Synthesis: (a) Fujimoto, Y.; Yokura, S.; Nakamura, T.; Morikawa, T.; Tatsuno, T. Tetrahedron Lett. 1974, 2523-2526.
9. (b) Masuoka, N.; Kamikawa, T. Tetrahedron Lett. 1976, 1691-1694.
10. Hua, D. H.; Venkataraman, S.; King, R. C.-Y.; Paukstelis, J. V. J. Am. Chem. Soc. 1988, 110, 4741-4748.
11. Anderson, W. K.; Lee, G. E. J. Med. Chem. 1980, 23, 96-97.
12. Salmond, W. G.; Barta, M. A.; Havens, J. L. J. Org. Chem. 1978, 43, 2057-2059.
13. Stereochemistries of two isomers were tentatively assigned by NOE experiments after their conversions into 27 and 28, respectively. (Equation presented)
14. 2: C, 78, 01; H. 9.00%. Found: C, 77.63; H, 9.34%.
15. 2Si: C, 72.87; H, 10.56%. Found: C, 72.73; H, 10.52%.