A new stereocontrolled route to (+)-curcuphenol, a phenolic sesquiterpene from the marine sponge Didiscus flavus

Tetrahedron Asymmetry

Volumn 9, Issue 13, 1998, Pages 2215-2217

  Sugahara, Tsutomu ^a   Ogasawara, Kunio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; CURCUPHENOL; CYTOTOXIC AGENT; PHENOL DERIVATIVE; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG ISOLATION; DRUG SYNTHESIS; PRIORITY JOURNAL; SPONGE (PORIFERA); STEREOCHEMISTRY;

EID: 0032479249     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00234-1     Document Type: Article

References (25)

1. (a) Ogasawara, K. Pure & Appl. Chem. 1994, 66, 2119.
2. (b) Ogasawara, K. J. Syn. Org. Chem. Jpn 1996, 54, 15.
3. Sugahara, T.; Kuroyanagi, Y.; Ogasawara, K. Synthesis 1996, 1101.
4. Takano, S.; Sato, T.; Inomata, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1991, 462.
5. Nakada, Y.; Sugahara, T.; Ogasawara, K. Tetrahedron Lett. 1997, 38, 857.
6. Pertinent reviews: (a) Mitsunobu, O. Synthesis 1981, 1.
7. (b) Hughes, D. L. Org. React. 1992, 42, 335.
8. (c) Hughes, D. L. Org. Prep. Proc. Int. 1996, 28, 127.
9. (a) Goering, H. L.; Kimoto, W. I. J. Am. Chem. Soc. 1965, 87, 1748.
10. (b) Takano, S.; Akiyama, M.; Ogasawara, K. J. Chem. Soc., Perkin Trans. 1 1985, 2447.
11. Shull, B. K.; Sakai, T.; Nichols, J. B.; Koreeda, M. J. Org. Chem. 1997, 62, 8294.
12. Wright, A. E.; Pomponi, S. A.; McConnell, O. J.; Kohmoto, S.; McCarthy, P. J. J. Nat. Prod. 1987, 50, 976.
13. (-)-Curcuphenol was also isolated from the Caribbean gorgonian Pseudopterogorgia rigida, see: McEnroe, F. J.; Fenical, W. Tetrahedron 1978, 34, 1661.
14. Isolation of curcuphenol with undetermined absolute structure from a terrestrial plant was also reported, see: Bohlmann, F.; Lonitz, M. Chem. Ber. 1978, 111, 843.
15. Synthesis of curcuphenol: racemic: Ref. 9; chiral for (-)-enantiomer: Ghisalberti, E. L.; Jefferies, P. R.; Stuart, A. D. Aust. J. Chem. 1979, 32, 1627.
16. iOH-hexane).
17. (a) Rhoads, S. J.; Raulins, N. R. Org. React. 1975, 22, 1.
18. (b) Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Paquette, L. A., Eds; Pergamon Press: Oxford, 1991; Vol. 5, p. 827.
19. Fleming, I. In Frontier Orbitals and Organic Chemical Reactions; John Wiley & Sons: London, 1976.
20. Vdovtsova, E. A. Zh. Org. Khim. 1969, 5, 498 [Chem. Abstr. 1969, 71, 12719V].
21. Vdovtsova, E. A. Zh. Org. Khim. 1969, 5, 498 [Chem. Abstr. 1969, 71, 12719V].
22. Miyashita, M.; Yoshikoshi, A.; Grieco, P. A. J. Org. Chem. 1977, 42, 3772.
23. Parikh, J. R.; Doering, W. v. E. J. Am. Chem. Soc. 1967, 89, 5505.
24. Heerden, F. R. v.; Zyl, J. J. v.; Rall, G. J. H.; Brandt, E. V.; Roux, D. G. Tetrahedron Lett. 1978, 661.
25. Guanti, G.; Narisano, E.; Podgorski, T.; Thea, S.; Williams, A. Tetrahedron 1990, 46, 7081.