Work

Stereoselective Synthesis of Both Tetrahydropyran Rings of the Antitumor Macrolide, (−)-Lasonolide A

Year: 2012

Type: article

Abstract: Stereoselective syntheses of both functionalized tetrahydropyran subunits of (-)-lasonolide A are described. These tetrahydropyran rings were constructed using catalytic asymmetric hetero Diels-Alder reactions as the key steps. The C22 quaternary stereocenter present in the upper tetrahydropyran ring was constructed by a stereoselective alkylation, and the C9 hydroxy stereochemistry of the bottom tetrahydropyran was constructed by a stereoselective epoxidation followed by a regioselective epoxide opening reaction.

Source: The Journal of Organic Chemistry

DOI: 10.1021/jo202631e

Authors: Arun K. Ghosh, Guo-Bao Ren

Institution: Purdue University West Lafayette

Language: English

Topic: Organic Chemistry Synthesis Methods

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

Awards: DESIGN AND SYNTHESIS OF NONPEPTIDE PROTEASE INHIBITORS, Design & Synthesis of Nonpeptide Protease Inhibitors