Title
The Chemical Synthesis of the 1-C-Alkyl Substituted Pyrrolidine and Piperidine Iminosugar Natural Products and their Analogues
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.
Open Access Status
This publication is not available as open access
Volume
26
Issue
23
First Page
2071
Last Page
2097
Funding Number
DP130101968
Funding Sponsor
Australian Research Council