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Communication | Special issue | Vol 73, No. 1, 2007, pp.217-225
Published online, 28th August, 2007
DOI: 10.3987/COM-07-S(U)36
Total Synthesis of (±)-Komaroviquinone

George Majetich,* Yang Li, and Ge Zou

*Department of Chemistry, The University of Georgia, Athens, Georgia 30602, U.S.A.

Abstract

(±)-Komaroviquinone (1) was synthesized from 3,4,5-trimethoxybenzoic acid in twenty-two steps. The key transformations in this synthesis are: (1) the construction of the cycloheptane ring via a Friedel-Crafts cyclialkylation; (2) a regiospecific benzylic oxidation; (3) a conformationally controlled introduction of the C(10) hydroxyl group and (4) intramolecular hemi-acetal formation.