Journal article
Versatile configuration-encoded strategy for rapid synthesis of 1,5-polyol stereoisomers
Organic letters, Vol.12(21), pp.5016-5019
11/05/2010
DOI: 10.1021/ol1021417
PMID: 20939544
Abstract
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.
Details
- Title: Subtitle
- Versatile configuration-encoded strategy for rapid synthesis of 1,5-polyol stereoisomers
- Creators
- Gregory K Friestad - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, United States. gregory-friestad@uiowa.eduGopeekrishnan Sreenilayam
- Resource Type
- Journal article
- Publication Details
- Organic letters, Vol.12(21), pp.5016-5019
- Publisher
- United States
- DOI
- 10.1021/ol1021417
- PMID
- 20939544
- ISSN
- 1523-7060
- eISSN
- 1523-7052
- Language
- English
- Date published
- 11/05/2010
- Academic Unit
- Chemistry
- Record Identifier
- 9983985922902771
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