YAKUGAKU ZASSHI
Online ISSN : 1347-5231
Print ISSN : 0031-6903
ISSN-L : 0031-6903
Stereochemical Studies. XXXII. Asymmetric Synthesis of Intermediates for the Total Synthesis of Steroids and Terpenes with L-Proline Enamine Method
KAZUO NAGASAWAHISANORI TAKAHASHIKUNIO HIROISHUN-ICHI YAMADA
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JOURNAL FREE ACCESS

1975 Volume 95 Issue 1 Pages 33-45

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Abstract
(S)-(+)-8-methyl-5, 6, 7, 8-tetrahydroindane-1, 5-dione (VI) and (S)-(+)-8a-methyl-1, 2, -3, 5, 6, 7, 8, 8a-octahydro-3, 8-naphthalenedione (VII) were asymmetrically synthesized from 2-methylcyclopentane-1, 3-dione (IV) and 2-methylcyclohexane-1, 3-dione (V) using L-proline derivatives. Asymmetric synthesis of VI or VII from 2-methyl-2- (3-oxobutyl) cyclorentane-1, 3-dione (X) or 2-methyl-2- (3-oxobutyl) cyclohexane-1, 3-dione (XI) was also carried out under various reaction conditions. The reaction path of this asymmetric synthesis is discussed.
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