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PMID: 16562928 Published · ppublish English Journal Article Research Support, N.I.H., Extramural Research Support, Non-U.S. Gov't

Total synthesis and biological evaluation of 11-desmethyllaulimalide, a highly potent simplified laulimalide analogue.

Organic letters ·Vol. 8 ·No. 7 ·2006-03-30 ·Pages 1507-10

Wender PA, Hilinski MK, Soldermann N, Mooberry SL

Abstract

[reaction: see text] A step-economical synthesis of 11-desmethyllaulimalide (2) is reported. This simplified analogue is available through an improved second-generation synthetic approach to the laulimalides, in a shorter step count and from much less expensive starting material than the parent compound. This new lead retains the anticancer function of laulimalide.

MeSH Terms

Antineoplastic Agents/chemical synthesis,chemistry,economics,pharmacology Drug Screening Assays, Antitumor HeLa Cells Humans Inhibitory Concentration 50 Macrolides Molecular Structure Paclitaxel/pharmacology Structure-Activity Relationship Taxoids/chemical synthesis,chemistry,economics,pharmacology

Chemicals

11-desmethyllaulimalide Antineoplastic Agents Macrolides Taxoids laulimalide Paclitaxel

Authors & Affiliations

4 authors, click to expand affiliations / ORCID

Wender Paul A

Departments of Chemistry and Molecular Pharmacology, Stanford University, Stanford, California 94305-5080, USA. wenderp@stanford.edu

Hilinski Michael K

Soldermann Nicolas

Mooberry Susan L

Article Info

Journal

Organic letters

Abbr.

Org Lett

ISSN

1523-7060

DOI

10.1021/ol060233g

wenderp@stanford.edu

Published

2006-03-30

Pages

1507-10

Language

English

Region

United States

NLM ID

100890393

Subset

Grants

NCI NIH HHS · CA31841 · United States

External Links

PubMed source DOI: 10.1021/ol060233g View journal details

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Total synthesis and biological evaluation of 11-desmethyllaulimalide, a highly potent simplified laulimalide analogue.

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