Formal syntheses of (-)-.ALPHA.- and (+)-.BETA.-cuparenones, cuparene, and laurene.
- 1 January 1988
- journal article
- Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN
- Vol. 36 (4) , 1379-1385
- https://doi.org/10.1248/cpb.36.1379
Abstract
This paper describes formal syntheses of the title compounds from the easily prepared chiral synthon (+)-5. One of the structural features of the cuparene family is the presence of vicinal quaternary carbons on the five-membered ring. The quaternary carbon with the tolyl function could be constructed by stereoselective 1, 4-addition of (p-tolyl)2 Zn to(+)-5. The key intermediate β-ketol (13), obtained from (+)-5 via a sequence of reactions, was successfully applied to formal syntheses of the title compounds.Keywords
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