First total synthesis and absolute configuration of marine cembrane diterpenoid (+)-11,12-epoxysarcophytol A

Tetrahedron Letters

Volumn 41, Issue 13, 2000, Pages 2181-2184

  Lan, Jiong ^a   Liu, Zuosheng ^a   Yuan, Hao ^a   Peng, Lizeng ^a   Li, Wei Dong Z ^a   Li, Ying ^a   Li, Yulin ^a   Chan, Albert S C ^b  

^a LANZHOU UNIVERSITY   (China)

^b HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENOID; SARCOPHYTOL A;

ARTICLE; CYCLIZATION; DRUG CONFORMATION; DRUG SYNTHESIS; ENANTIOMER; EPOXIDATION; STEREOCHEMISTRY;

ALCYONACEA; ANTHOZOA; LOBOPHYTUM;

EID: 0034719802     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00129-5     Document Type: Article

References (22)

1. Tursch, B.; Braeckamn, J. C.; Dolaze, D.; Kaisin, M. In Marine Natural Products: Chemical and Biological Perspectives; Scheuer, P. J., Ed.; Academic Press: New York, 1978; Vol. 2, pp. 286-387.
2. (a) Tius, M. A. Chem. Rev. 1988, 88, 719-732;
3. (b) Cox, N. J. G.; Mills, S. D.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1992, 1313-1321, and references cited therein.
4. Bowden, B. F.; Coll, J. C.; Tapiolas, D. M. Aust. J. Chem. 1983, 36, 2289-2295.
5. (a) Kobayashi, M.; Nakagawa, T.; Mitsuhashi, H. Chem. Pharm. Bull. 1979, 27, 2382-2387;
6. (b) Blackman, A. J.; Bowden, B. F.; Coll, J. C.; Frick, B.; Mahendran, M.; Mitchell, S. J. Aust. J. Chem. 1982, 35, 1873-1880.
7. Li, W.-D. Z.; Li, Y.; Li, Y.-L. Tetrahedron Lett. 1999, 40, 965-968.
8. (a) Takayanagi, H.; Kitano, Y.; Morinaka, Y. J. Org. Chem. 1994, 59, 2700-2706;
9. (b) idem, Tetrahedron Lett. 1990, 31, 3317-3320.
10. (a) Yue, X.-J.; Li, Y.-L.; Sun, Y.-J. Bull. Soc. Chim. Belgium 1995, 104, 509;
11. (b) Yue, X.-J.; Li, T.-H.; Li, Y.-L. Chinese Chem. Lett. 1995, 6, 189-192.
12. (a) Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974-5976;
13. (b) Wang, Z.-M.; Zhou, W.-S. Tetrahedron 1987, 43, 2935-2944; for applications in natural product synthesis, see: Pfenninger, A. Synthesis 1986, 89-116.
14. (b) Wang, Z.-M.; Zhou, W.-S. Tetrahedron 1987, 43, 2935-2944; for applications in natural product synthesis, see: Pfenninger, A. Synthesis 1986, 89-116.
15. (a) Raggio, M. L.; Watt, D. S. J. Org. Chem. 1976, 41, 1873-1875;
16. (b) Freerksen, R. W.; Selikon, S. J.; Wroble, R. R.; Kyler, K. S.; Watt, D. S. J. Org. Chem. 1983, 48, 4087-4096, and references cited therein.
17. Takayanagi, H. Tetrahedron Lett. 1994, 35, 1581-1584.
18. +]: 304.2397; found: 304.2392.
19. Evans, D. A.; Hoffman, J. M.; Truesdale, L. K. J. Am. Chem. Soc. 1973, 95, 5822-5823.
20. Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1986-2012, and references cited therein.
21. Masui, M.; Shioiri, T. Synlett 1997, 273-274.
22. Authentic samples of natural product 1 and its acetate were not available for direct comparisons.