Publication Name

Current Organic Chemistry

Abstract

A review of the chemical synthesis of the 1-C-alkyl substituted pyrrolidine and piperidine iminosugar natural products and their analogues (where the alkyl chain comprises two or more car-bons) is provided. These syntheses can be grouped into nine different synthetic strategies that share a common approach toward installing the alkyl substituent. These include nucleophilic addition to al-dimines; Grignard additions to glycosylamines, cyclic imides, and carbohydrates; Weinreb ketone synthesis; nucleophilic addition to cyclic nitrones; the Overmann rearrangement; the allylation of hemiaminals; and the Petasis borono-Mannich reaction. The broussonetine alkaloids have proven popular synthetic targets to develop new synthetic methods and verify these target molecules' struc-tures and stereochemistry.

Volume

26

Issue

23

First Page

2071

Last Page

2097

Funding Number

DP130101968

Funding Sponsor

Australian Research Council

Available for download on Saturday, February 03, 2024

COinS
 

Link to publisher version (DOI)

http://dx.doi.org/10.2174/1385272827666230124150741