Total synthesis of (R,R,R)- and (S,S,S)-schweinfurthin F: Differences of bioactivity in the enantiomeric series

Nolan R. Mente; Andrew J. Wiemer; Jeffrey D. Neighbors; John A. Beutler; Raymond J. Hohl; David F. Wiemer

doi:10.1016/j.bmcl.2006.11.096

Total synthesis of (R,R,R)- and (S,S,S)-schweinfurthin F: Differences of bioactivity in the enantiomeric series

Nolan R. Mente
, Andrew J. Wiemer
, Jeffrey D. Neighbors
, John A. Beutler
, Raymond J. Hohl
, David F. Wiemer

Research output: Contribution to journal › Article › peer-review

42 Scopus citations

Abstract

Total synthesis of the (R,R,R)- and (S,S,S)-enantiomers of the natural product schweinfurthin F has been completed. Comparisons of spectral data and optical rotations with those reported for the natural product, as well as a variety of bioassay data, allow assignment of the natural material as the (R,R,R)-isomer.

Original language	English (US)
Pages (from-to)	911-915
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	17
Issue number	4
DOIs	https://doi.org/10.1016/j.bmcl.2006.11.096
State	Published - Feb 15 2007

All Science Journal Classification (ASJC) codes

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmcl.2006.11.096

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author = "Mente, \{Nolan R.\} and Wiemer, \{Andrew J.\} and Neighbors, \{Jeffrey D.\} and Beutler, \{John A.\} and Hohl, \{Raymond J.\} and Wiemer, \{David F.\}",

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T2 - Differences of bioactivity in the enantiomeric series

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AU - Wiemer, Andrew J.

AU - Neighbors, Jeffrey D.

AU - Beutler, John A.

AU - Hohl, Raymond J.

AU - Wiemer, David F.

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AB - Total synthesis of the (R,R,R)- and (S,S,S)-enantiomers of the natural product schweinfurthin F has been completed. Comparisons of spectral data and optical rotations with those reported for the natural product, as well as a variety of bioassay data, allow assignment of the natural material as the (R,R,R)-isomer.

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Total synthesis of (R,R,R)- and (S,S,S)-schweinfurthin F: Differences of bioactivity in the enantiomeric series

Abstract

All Science Journal Classification (ASJC) codes

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