Synthesis of Scaffolds with Glycomimetic Structures

C.      Gravier-Pelletier; Y.      Le Merrer

doi:10.2174/157017907779981624

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

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Current Organic Synthesis

Title: Synthesis of Scaffolds with Glycomimetic Structures

Volume: 4 Issue: 1

Author(s): C. Gravier-Pelletier and Y. Le Merrer

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

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.

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Gravier-Pelletier C. and Le Merrer Y., Synthesis of Scaffolds with Glycomimetic Structures, Current Organic Synthesis 2007; 4 (1) . https://dx.doi.org/10.2174/157017907779981624