Synthesis of optically active bicyclo[3.3.0]octane Skeleton using transannular reaction

DOI: 10.1248/cpb.46.17

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 17 - 21 (1998)

Update date:2022-08-29

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Authors:

Horikawa, Tamaki

Norimine, Yoshihiko

Tanaka, Masakazu

Sakai, Kiyoshi

Suemune, Hiroshi

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Article abstract of DOI:10.1248/cpb.46.17

Optically active 5-cyclooctene-1,2-diol derivatives prepared by an enzymatic procedure have been converted into bicyclo[3.3.0]octane derivatives by transannular reaction with complete inversion of the stereogenic center linked to the leaving group. Formal synthesis of (+)-iridomyrmecin has been achieved starting from (S,S)-5-cyclooctene-1,2-diol by using this process.

Full text of DOI:10.1248/cpb.46.17

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