Stereoselective Synthesis of Tricyclo[6.2.2.0^2,7]dodecane-3,6,9,10-tetrol via Selective Reduction of α,β-Unsaturated 1,4-DIKetone

Abstract

Stereoselective synthesis of tricyclo[6.2.2.0^2,7]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.

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GRAPHICAL ABSTRACT

Keywords:

• Cyclitol
• polyhydroxylated compound
• reduction of α,β-unsaturated 1,4-diketone
• tricyclic tetrol