Work

Enantioselective total synthesis of macrolide (+)-neopeltolide

Year: 2013

Type: article

Abstract: The asymmetric total synthesis of the anti-proliferative macrolide (+)-neopeltolide has been completed. The stereochemically defined trisubstituted tetrahydropyran ring was constructed via a catalytic hetero-Diels-Alder reaction creating two new chiral centers in a highly diastereoselective manner. The other key features of this synthesis included Brown's asymmetric allylation to install the requisite C-11 and C-13 stereocenters. The synthesis of the oxazole side chain consisted of a hydrozirconation of an alkynyl stannane to establish the Z stereochemistry, followed by a palladium catalyzed cross coupling to introduce the desired Z olefin in the oxazole side chain.

Source: Organic & Biomolecular Chemistry

DOI: 10.1039/c3ob41541d

Authors: Arun K. Ghosh, Khriesto A. Shurrush, Zachary L. Dawson

Institution: Purdue University West Lafayette

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Purdue University, National Institutes of Health, National Institute of General Medical Sciences

Award: DESIGN AND SYNTHESIS OF NONPEPTIDE PROTEASE INHIBITORS