Formal Syntheses of (-)-α- and (+)-β-Cuparenones, Cuparene, and Laurene

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 constructe...

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Bibliographic Details
Published inChemical & pharmaceutical bulletin Vol. 36; no. 4; pp. 1379 - 1385
Main Authors OKANO, KOUJI, SUEMUNE, HIROSHI, SAKAI, KIYOSHI
Format Journal Article
LanguageEnglish
Published Tokyo The Pharmaceutical Society of Japan 1988
Maruzen
Subjects
(+)-β-cuparenone
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
Terpenoids
Hydrocarbon
Enantiomer
Sesquiterpenes
Ketol
Diester
Addition reaction
Chiral compound
Ketoester
Monocyclic compound
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Summary: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.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.36.1379