Format

Send to

Choose Destination
J Am Chem Soc. 2009 Sep 2;131(34):12406-14. doi: 10.1021/ja904604x.

Total synthesis and structure-activity investigation of the marine natural product neopeltolide.

Author information

1
Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Northwestern University, Evanston, Illinois 60208, USA.

Abstract

The total synthesis and biological evaluation of neopeltolide and analogs are reported. The key bond-forming step utilizes a Lewis acid-catalyzed intramolecular macrocyclization that installs the tetrahydropyran ring and macrocycle simultaneously. Independent of each other, neither the macrolide nor the oxazole side chain substituents of neopeltolide can inhibit the growth of cancer cell lines. The biological data of the analogs indicate that alterations to either the ester side chain or the stereochemistry of the macrolide result in a loss of biological activity.

PMID:
19663512
PMCID:
PMC2735232
DOI:
10.1021/ja904604x
[Indexed for MEDLINE]
Free PMC Article

Supplemental Content

Full text links

Icon for American Chemical Society Icon for PubMed Central
Loading ...
Support Center