Work

Total Synthesis of (−)-18-epi-Peloruside A: An Alkyne Linchpin Strategy

Year: 2013

Type: article

Abstract: A convergent synthetic route toward cytotoxic agent peloruside A that hinges on the use of an alkyne linchpin to assemble the natural product is described. Other highlights of this synthesis include an asymmetric desymmetrization reaction of a 1,3-diol, a one-pot conversion of a dibromoolefin to a stereodefined enone, and a diastereoselective aldol condensation. Misassignment of the absolute stereochemistry of the C18 stereocenter in our synthesis provided the natural product epimeric at the C18 ethyl stereocenter.

Source: Organic Letters

DOI: 10.1021/ol4024997

Authors: Barry M. Trost, David J. Michaelis, Sushant Malhotra

Institution: Stanford University

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: Novel Approaches for Antitumor and Antiviral Agents, G3811411720, Total Synthesis of Cytotoxic ent-Kauranoid Natural Products