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Preparation of Bicyclo[3.3.0]octane-2,8-dione- and Declain-1,8-dione-Derivatives

✍ Scribed by Rudolf O. Duthaler; Peter Maienfisch

Publisher
John Wiley and Sons
Year
1984
Tongue
German
Weight
596 KB
Volume
67
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Alkylation of bicyclo[3.3.0]octane‐2,8‐dione (1), which is prepared by a modification of the procedure described in the literature, gives the methyl‐ and propynyl‐derivatives 6 and 7 (Scheme 1). In addition to the method described previously (Scheme 2), 9‐methyl‐cis‐decalin‐1,8‐dione 9 is obtainable stereoselectively either by cyclization of keto‐acid 16, or by aldol cyclization of keto‐aldehyde 26 and oxydation of the resulting alcohols 24 and 25 (Scheme 4). The β‐keto‐alcohols 24 and 25 undergo a base‐catalyzed isomerization; the trans‐decalin isomers 27 and 28 are not detected in this equilibrium mixture (Schemes 4 and 5)l. Monoreduction of cis‐dione 9 gives the endo‐alcohol 25, while 27 is the favored product of the reductin of trans‐dione 10 (Scheme 4). Optically pure (+)‐25 can be prepared from (9__S__,10__R__)‐monoacetal 29 (Scheme 5).

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