Work

A Convergent Synthesis of the Proposed Structure of Antitumor Depsipeptide Stereocalpin A

Year: 2009

Type: article

Abstract: The total synthesis of the proposed structure of anticancer agent stereocalpin A is described. The synthesis features a diastereoselective synthesis of a 5-hydroxy-2,4-dimethyl-3-oxooctanoic acid unit with asymmetric anti- and syn-aldol reactions as the key steps. Initial cycloamidation led to complete epimerization at the C-11 stereocenter due to unique steric constraints in the 12-membered depsipeptide ring. A late-stage methylation strategy led to the synthesis of the proposed structure of stereocalpin A.

Source: Organic Letters

DOI: 10.1021/ol900412u

Authors: Arun K. Ghosh, Chun-Xiao Xu

Institution: Purdue University West Lafayette

Language: English

Topic: Chemical Synthesis and Analysis

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

SDG: Good health and well-being

Open Access status: green

Funder: National Institute of General Medical Sciences