Total Synthesis of Peribysin E Necessitates Revision of the Assignment of its Absolute Configuration | Zendy

Angeles Angie R. | Zendy; Dorn David C. | Zendy; Kou Cynthia A. | Zendy; Moore Malcolm A. S. | Zendy; Danishefsky Samuel J. | Zendy

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Total Synthesis of Peribysin E Necessitates Revision of the Assignment of its Absolute Configuration

Author(s) -

Angeles Angie R.,

Dorn David C.,

Kou Cynthia A.,

Moore Malcolm A. S.,

Danishefsky Samuel J.

Publication year - 2007

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200604308

Subject(s) - absolute configuration , computer science , stereochemistry , enantiomer , chemistry , content (measure theory) , mathematics , mathematical analysis

The right way round : Peribysin E, a naturally occurring adhesion inhibitor, has been synthesized and, as a result, its absolute configuration reassigned. The natural and nonnatural enantiomers can be reached starting from ( R )‐ or ( S )‐carvone, respectively. A key step is the ring contraction of 1 to 2 (see scheme, TBS= tert ‐butyldimethylsilyl, TES=triethylsilyl).

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