Synthesis of Scaffolds with Glycomimetic Structures

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 C 2 -symmetrical bis-epoxides derived from D-mannitol. The described strategy permits access to various configurations of these scaffolds.

Stereoselective Synthesis of 3-Aryloctahydroindoles and Application in a Formal Synthesis of (−)-Pancracine

“…For example, the octahydroindole motif is found in several bioactive natural products such as the Amaryllidaceae and sceletium , alkaloids and also the aeruginosins . Recently, applications of octahydroindole scaffolds in the diversity-oriented synthesis of Amaryllidaceae alkaloid type structures, glycomimetics, and glycosidase inhibitors have been reported. The stereochemistry of the ring junction in the octahydroindole influences its biological profile.…”