TOTAL SYNTHESIS OF (+/-)PENTALENENE, (+/-)-PENTALENIC ACID, AND (+/-)-DEOXYPENTALENIC ACID THROUGH AN INTRAMOLECULAR DOUBLE MICHAEL REACTION

DOI: 10.1039/P19880002963

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2963 - 2970 (1988)

Update date:2022-08-03

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Authors:

Ihara,Masataka

Katogi, Mamoru

Fukumoto, Keiichiro

Kametani, Tetsuji

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Article abstract of DOI:10.1039/P19880002963

The angular triquinane sesquiterpenes, (+/-)-pentalenene (1), (+/-)-pentalenic acid (2), and (+/-)-deoxypentalenic acid (4), were synthesized via the intramolecuar double Michael reaction as the key step.Heating the bis-enone (10), prepared from 4,4-dimethylcyclopent-2-enene (11) in six steps, with chlorotrimethylsilane, triethylamine, and zinc chloride gave the tricyclo<7,3,0,0^1,5>dodecanedione (9), which was converted into the above triquinanes after ring contraction.

Full text of DOI:10.1039/P19880002963

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