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

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.

SUBMITTER: Shang S

PROVIDER: S-EPMC2597797 | biostudies-literature | 2007 May

REPOSITORIES: biostudies-literature

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

Shang Shiying S Iwadare Hayato H Macks Daniel E DE Ambrosini Lisa M LM Tan Derek S DS

Organic letters 20070417 10

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 u ...[more]

PMID: 17439132

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