Synthesis of (+)-Voglibose
Camille Rocq1, Vincent Hamel1, Alexandra Furtos-Matei2
1Laboratoire de Méthodologie et Synthèse de Produits Naturels, Université du Québec à Montréal, C.P. 8888, Succ. Centre-Ville, Montréal, H3C 3P8, Québec, Canada.
Abstract:
A concise asymmetric synthesis of voglibose, a natural product derivative and an alpha-glucosidase inhibitor with antihyperglycemic activity, was produced from an O-arylated lactic acid derivative in only seven steps. This approach was based on an oxidative phenol dearomatization process promoted by a hypervalent iodine reagent, a chiral auxiliary serving as a protecting group and allowing the asymmetric formation of the target, and a key hydrolysis leading to the formation of several contiguous stereocenters and removal of the chiral auxiliary.
Related Concept Videos
Insulin: Biosynthesis, Chemistry, and Preparation
Damage or functional impairment of β-cells inhibits insulin production, leading to diabetes. Diabetes treatment...
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Aldol Condensation with β-Diesters: Knoevenagel Condensation
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation


