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Org Lett. 2007 May 10;9(10):1895-8. Epub 2007 Apr 17.

A unified synthetic approach to polyketides having both skeletal and stereochemical diversity.

Author information

1
Pharmacology Program, Weill Graduate School of Medical Sciences of Cornell University, Memorial Sloan-Kettering Cancer Center, New York, NY 10021, USA.

Abstract

An efficient systematic approach to the diversity-oriented synthesis of polyketides has been developed to provide both skeletal and stereochemical diversity. Each synthetic intermediate is also a desired polyketide fragment and no protecting group manipulations are required. A first-generation synthesis provides a 74-membered polyketide library comprising six different skeletal classes, each in one to five steps from propargylic alcohol precursors. A study of epoxyol opening reactions revealed unusual reactivity trends based on epoxide configuration.

PMID:
17439132
PMCID:
PMC2597797
DOI:
10.1021/ol070405p
[Indexed for MEDLINE]
Free PMC Article

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