Stereoselective Synthesis of Tricyclo[6.2.2.02,7]dodecane-3,6,9,10-tetrol via Selective Reduction of α,β-Unsaturated 1,4-DIKetone

Author： Kelebekli Latif  

Publisher： Taylor & Francis Ltd

ISSN： 0039-7911

Source： Synthetic Communications, Vol.43, Iss.22, 2013-11, pp. : 2998-3009

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Abstract

Stereoselective synthesis of tricyclo[6.2.2.02,7]dodecane-3,6,9,10-tetrol was developed starting from p-benzoquinone. The endo selective Diels–Alder cycloaddition of p-benzoquinone and 1,3-cyclohexadiene afforded the corresponding bicyclic diketone. The synthesis of the title compound was based on the cycloadduct by selective reduction with NaBH4, acetylation with AcCl, and hydroxylation with OsO4-NMO.[Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource: Full experimental and spectral details.]

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