Abstract

Efficient and total synthesis of enantiopure cyclitols with a C6, C7 or C8 ring as framework and related aminocyclitols, including polyhydroxylated octahydroindoles and decahydroquinolines are reported from C2-symmetrical bis-epoxides derived from D-mannitol. The described strategy permits access to various configurations of these scaffolds.

Keywords: Carbacycles, aminocyclitols, epoxide opening, ring closing metathesis, Brook rearrangement, reductive amination