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 journalArticle

33 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)911-915
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume17
Issue number4
DOIs
StatePublished - Feb 15 2007

Fingerprint

Bioactivity
Biological Products
Optical rotation
Optical Rotation
Enantiomers
Bioassay
Isomers
Biological Assay
schweinfurthin F

All Science Journal Classification (ASJC) codes

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

Cite this

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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.",
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Total synthesis of (R,R,R)- and (S,S,S)-schweinfurthin F : Differences of bioactivity in the enantiomeric series. / Mente, Nolan R.; Wiemer, Andrew J.; Neighbors, Jeffrey D.; Beutler, John A.; Hohl, Raymond J.; Wiemer, David F.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 17, No. 4, 15.02.2007, p. 911-915.

Research output: Contribution to journalArticle

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AU - Mente, Nolan R.

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AU - Neighbors, Jeffrey D.

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AU - Hohl, Raymond J.

AU - Wiemer, David F.

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