A Common Synthetic Protocol for the Cyclic and Acyclic Core of Migrastatin, Isomigrastatin, and Dorrigocin via a Chiral β‐Hydroxy‐γ‐butyrolactone Intermediate. Issue 29 (26th August 2014)

• Record Type: Journal Article
• Authors: Gade, Narendar Reddy; Iqbal, Javed
• Is Part Of: European journal of organic chemistry. Issue 29(2014)
• Page Start: 6558
• Page End: 6564
• Publication Date: 2014-08-26
• Subjects: Synthesis design -- Metathesis -- C–H activation -- Oxidation -- Natural products -- Lactones; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201402830
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A facile synthetic route has been developed for the synthesis of the cyclic and acyclic cores of migrastatin, isomigrastatin, and dorrigocin. The common synthetic route goes via a β‐hydroxy‐γ‐butyrolactone intermediate that is obtained by a Pd II ‐catalysed asymmetric allylic intramolecular cyclization of 3‐hydroxy‐2‐methylhex‐5‐enoic acid following a protocol developed by White and coworkers. Abstract : The synthesis of a key intermediate chiral β‐hydroxy‐γ‐butyrolactone (A) by Pd II ‐catalysed stereoselective allylic C–H oxidation is reported. A common synthetic route to transform this intermediate into key building blocks for the synthesis of migrastatin family members has been developed.