Total Synthesis of d,l-Isospongiadiol: An Intramolecular Radical Cascade Approach to Furanoditerpenes
The Journal of Organic Chemistry1996Vol. 61(5), pp. 1806–1813
Citations Over TimeTop 10% of 1996 papers
Abstract
A stereoselective oxidative free-radical cyclization of beta-keto ester polyenes 7 and 19 has been accomplished as a one-step entry to the tricarbocyclic synthons 8and 21 which contain five and six stereogenic centers, respectively. These key synthons possessing an axial carboethoxy group at C-4 were ultimately converted to the spongian skeleton (8--> 14 and 21 --> 25 -->14). The synthesis of d,l-isospongiadiol (3) from the common intermediate 14 was realized after introduction of the 2alpha-hydroxy group in the spongian A-ring via epoxidation of silyl enol ether 28 and subsequent desilylation.
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