1. A Unified Synthetic Approach to Polyketides Having Both Skeletal and Stereochemical Diversity
- Author
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Derek S. Tan, Lisa M. Ambrosini, Hayato Iwadare, Daniel E. Macks, and Shiying Shang
- Subjects
Molecular Structure ,Stereochemistry ,Organic Chemistry ,Epoxide ,Stereoisomerism ,Methylation ,Biochemistry ,Carbon ,Article ,chemistry.chemical_compound ,Polyketide ,chemistry ,Epoxy Compounds ,Macrolides ,Physical and Theoretical Chemistry ,Protecting group - 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.
- Published
- 2007
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