Journal
ORGANIC LETTERS
Volume 12, Issue 21, Pages 5016-5019Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol1021417
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Funding
- University of Iowa
- Graduate College Fellowship
- Faculty Scholar Award
- MPSFP
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The isolated stereogenic centers of 1,5-polyol-containing natural products present challenges to synthesis and structure determination. To address this problem, a configuration-encoded strategy defines each configuration within a simple 4-(arylsulfonyl)butyronitrile building block, a repeat unit that is reliably and efficiently coupled in iterative fashion to afford 1,5-polyols of defined stereochemistry. For example, the C27-C40 subunit of tetrafibricin is prepared in five steps and 42% yield. This strategy is amenable to rapid and unambiguous preparation of all configurational permutations of 1,5-polyols with equal facility.
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