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A novel diastereoselective synthesis of the lactone moiety of compactin

✍ Scribed by Kapa Prasad; Oljan Repič

Publisher
Elsevier Science
Year
1984
Tongue
French
Weight
186 KB
Volume
25
Category
Article
ISSN
0040-4039

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✦ Synopsis

A new synthesis of racemic $-hydroxy-&lactone 10 with requisite relative stereochemistry as in compactin (la) is described utilizing cis-cyclohexane-1,3,5-trio1 (2) as the starting material. Compactin' (la) and mevinolin* -(lb) have attracted a great deal of interest from synthetic organic chemists3 because of the high degree of complexity incorporated in their structures and due to their potent inhibition of HMG-CoA reductase, the rate-limiting enzyme in cholesterol biosynthesis.4 We present in laR=H 2 2 R = CH3

this communication a simple and practical stereoselective route to the 8-hydroxy-&lactone moiety' which is the common structural feature essential for the observed biological activity of the above natural products.

Our synthetic strategy is based upon the retrosynthetic analysis shown below, envisioning that the e-hydroxy-6-lactone could be derived from ciscyclohexane-1,3,5-triol.

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