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Communication | Special issue | Vol 76, No. 2, 2008, pp.1011-1016
Published online, 19th May, 2008
DOI: 10.3987/COM-08-S(N)70
A Simple Desymmetrization Approach to the Spiroxin Framework

Kazuyuki Nabatame, Masahiro Hirama, and Masayuki Inoue*

*Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Tokyo, Japan

Abstract

The highly strained hexacyclic framework of spiroxins, a family of 1,8-dihydroxynaphthalene-derived natural products, was efficiently constructed in ten steps from commercially available naphthalene-1,5-diol using a symmetry-based strategy. Key reactions in this synthesis are biaryl homocoupling, oxidative desymmetrization of a C2-symmetric intermediate, selective oxidation of the naphthalene portion, and oxidative cyclization.