Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
A Synthesis of α-Methylene-γ-lactones Fused to Medium and Large Rings by Intramolecular Cyclization of Formylated Allyl Halides
Kiyoshi NISHITANIMasashi ISOZAKIKoji YAMAKAWA
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1990 Volume 38 Issue 1 Pages 28-35

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Abstract

Carbocyclic rings fused to an α-methylene-γ-lactone unit were synthesized from ω-formylated β-ethoxycarbonylallyl halides (4a-g) through intramolecular cyclization by the use of a low-valent chromium reagent, prepared from CrCl3 and LiAlH4, in N, N-dimethylformamide. α-Methylene-γ-lactones fused to medium (eight-membered) or large (twelve-and fourteen-membered) ring system (5a, c and d) were synthesized by this method in good to fairly good yields. However, the formylated allyl halide (4b), expected to afford a ten-membered carbocyclic ring system, gave dilactones fused to a twenty-membered ring unit even under a high dilution reaction condition.

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© The Pharmaceutical Society of Japan
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