Work

Ex Chiral Pool Synthesis from a Highly Methyl-branched Wax Ester and Biological Properties of (+)-Capensifuranone

Year: 2009

Type: article

Abstract: Unnatural (+)-capensifuranone (+)-2 and its epimer (-)-5-epi-capensifuranone 6 were prepared from enantiopure methyl-branched aldehyde 4, employing cyclisation with 3-bromomethacrylic acid to 4-bromofuranones 5a,b followed by Negishi cross coupling. Compound 4 was obtained from the preen-gland wax-derived ester 3 after ozonolysis and reductive work-up. The configuration of 6 was determined via the X-ray crystal structure analysis of a derivative 10. Compounds (+)-2, 5a,b and 6 showed cytotoxic activity against L-929 mouse fibroblasts, and KB-3-1 HeLa and U-937 lymphoma cells.

Source: Zeitschrift für Naturforschung B

DOI: 10.1515/znb-2009-0608

Authors: Yana Galeyeva, Michael Morr, Florenz Sasse, Randi Diestel, Sabine Laschat, Angelika Baro, Wolfgang Frey

Institutions: University of Stuttgart, Helmholtz Centre for Infection Research

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $2,712

OpenAlex ID: W1986391918

FWCI: 0.323

Cites:

Cited by: 6

Related to: 10