Synthesis of (+)-sorokinianin

Tetrahedron Letters

Volumn 38, Issue 34, 1997, Pages 6015-6018

  Watanabe, Hidenori ^a   Onoda, Takahiro ^a   Kitahara, Takeshi ^a   Mori, Kenji ^b  

^a UNIVERSITY OF TOKYO   (Japan)

^b TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AGRICULTURAL CHEMICAL; SOROKINIANIN; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

HORDEUM VULGARE SUBSP. VULGARE;

EID: 0030837381     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01337-3     Document Type: Article

References (12)

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3. Nakajima, H.; Fujii M.; Toratsu, Y; Hamasaki, T.; Ichinoe, M. Abstract of papers, Annual Meeting of the Agricultural Chemical Society of Japan, Kyoto, April, 1996, p. 221.
4. Hagiwara, H.; Miyashita, M.; Uda, H.; Yoshikoshi, A. Bull. Chem. Soc. Jpn. 1975, 48, 3723-3726.
5. 4
6. Watanabe, H; Mori, K. J. Chem. Soc., Perkin Trans, I 1991, 2919-2934.
7. (a) Ruden, R. A.; Gaffney, B. L. Synth. Commun. 1975, 5, 15-19.
8. (b) Boeckman, Jr., R. K.; Silver, S. M. Tetrahedron Lett. 1973, 3497-3500.
9. Fetizon, M.; Golfier, M.; Louis, J.-M. Tetrahedron 1975, 31, 171-176.
10. Davis, F. A.; Vishwakarma, L. C; Billmers, J. M.; Finn, J. J. Org. Chem. 1984, 49, 3241-3243.
11. Interestingly, the Davis oxidation of a dianion prepared from 10 and 2 eq. of KHMDS gave only 2′-epi-1. The protection of the primary alcohol was therefore essential for the desired stereoselectivity.
12. 6: Nakajima, H. personal communication to H. W.