PHENYLDIMETHYLSILYL AS AN ALCOHOL SURROGATE IN INTRAMOLECULAR DIELS-ALDER CYCLOADDITION - SYNTHESIS OF ALPHA-DICTYOPTEROL

摘要

alpha-Dictyopterol (1a), a sesquiterpene isolated from the essential oil of Dicytopteris divaricata, has been synthesized from bicyclic ketone 2, obtained by thermal cyclization of triene intermediate 11. The key observation is that the phenyldimethylsilyl group, a surrogate for hydroxyl, does not interfere with the internal Diels-Alder cycloaddition. [References: 45]