Total synthesis of (±)-pentalenene, (±)-pentalenic acid, and (±)deoxypentalenic acid through an intramolecular double Michael reaction
- 1 January 1988
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 11,p. 2963-2970
- https://doi.org/10.1039/p19880002963
Abstract
The angular triquinane sesquiterpenes, (±)-pentalenene (1), (±)-pentalenic acid (2), and (±)-deoxypentalenic acid (4), were synthesized via the intramolecular double Michael reaction as the key step. Heating the bis-enone (10), prepared from 4,4-dimethylcyclopent-2-enone (11) in six steps, with chlorotrimethylsilane, triethylamine, and zinc chloride gave the tricyclo[7.3.0.0]dodecanedione (9), which was converted into the above triquinanes after ring contraction.Keywords
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