Ring Expansion of Cyclopropylmethanols to Cyclobutanes - An Enantioselective Total Synthesis of (R)-(+)-Dodecan-5-olide, and (S)-(+)- and (R)-(-)-5-dihydrofuran-2(3H)-one

DOI: 10.1039/P19900002835

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2835 - 2840 (1990)

Update date:2022-08-04

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Authors:

Nemoto, Hideo

Ishibashi, Hiroki

Mori, Masahiko

Fujita, Shigekazu

Fukumoto, Keiichiro

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Article abstract of DOI:10.1039/P19900002835

A novel and convenient route to chiral cyclobutanones (8) and (9) by ring expansion of the cyclopropylmethanols (6) and (7) was developed, leading to an enantioselective total synthesis of (R)-(+)-dodecan-5-olide (25), and (S)-(+)- and (R)-(-)-5-<(Z)-dec-1-enyl>dihydrofuran-2(3H)-one (35) and (36) (the pheromone of the Japanese beetle).

Full text of DOI:10.1039/P19900002835

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