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Semisynthetic Derivatives of Sesquiterpene Lactones by Palladium-Catalyzed Arylation of the α-Methylene-γ-lactone Substructure

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Changho Han†, Francis J. Barrios‡, Mark V. Riofski† and David A. Colby†‡

^† Department of Medicinal Chemistry and Molecular Pharmacology, Purdue University, West Lafayette, Indiana 47907

^‡ Department of Chemistry, Purdue University, West Lafayette, Indiana 47907

J. Org. Chem., 2009, 74 (18), pp 7176–7179

DOI: 10.1021/jo901533e

Publication Date (Web): August 21, 2009

dcolby@purdue.edu

Section:

Terpenes and Terpenoids

Abstract

The palladium-catalyzed arylation of different α-methylene-γ-lactone-containing sesquiterpene lactones was shown to produce E-olefin coupling products selectively in moderate to excellent yields. Biological evaluation of these semisynthetic sesquiterpene lactone derivatives in HeLa cells showed interesting antiproliferative profiles and provided initial structure−activity data.

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This article has been cited by 2 ACS Journal articles (2 most recent appear below).

Halocarbocyclization Entry into the Oxabicyclo[4.3.1]decyl Exomethylene-δ-Lactone Cores of Linearifolin and Zaluzanin A: Exploiting Combinatorial Catalysis
Sandeep K. Ginotra, Jacob A. Friest, and David B. Berkowitz
Organic Letters2012 Article ASAP
- Halocarbocyclization Entry into the Oxabicyclo[4.3.1]decyl Exomethylene-δ-Lactone Cores of Linearifolin and Zaluzanin A: Exploiting Combinatorial Catalysis
  Sandeep K. Ginotra, Jacob A. Friest, and David B. Berkowitz
  Organic Letters2012 Article ASAP
  A streamlined entry into the sesquiterpene lactone (SQL) cores of linearifolin and zaluzanin A is described. Stereochemistry is controlled through transformations uncovered by ISES (In Situ Enzymatic Screening). Absolute stereochemistry derives from ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Dialkylaluminum N,O-Dimethylhydroxylamine Complex as a Reagent to Mask Reactive Carbonyl Groups in Situ from Nucleophiles
Francis J. Barrios, Xuechao Zhang, and David A. Colby
Organic Letters2010 12 (23), 5588-5591
- Dialkylaluminum N,O-Dimethylhydroxylamine Complex as a Reagent to Mask Reactive Carbonyl Groups in Situ from Nucleophiles
  Francis J. Barrios, Xuechao Zhang, and David A. Colby
  Organic Letters2010 12 (23), 5588-5591
  Aluminum complexes of N,O-dimethylhydroxylamine are effective reagents to mask carbonyl groups in situ from nucleophilic addition by organolithiums, Grignard reagents, and borohydrides. The utility of this process by selectively adding nucleophiles into ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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History

Published In Issue September 18, 2009
Article ASAPAugust 21, 2009
Received: July 16, 2009

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Note

Semisynthetic Derivatives of Sesquiterpene Lactones by Palladium-Catalyzed Arylation of the α-Methylene-γ-lactone Substructure

Abstract

Citing Articles

Halocarbocyclization Entry into the Oxabicyclo[4.3.1]decyl Exomethylene-δ-Lactone Cores of Linearifolin and Zaluzanin A: Exploiting Combinatorial Catalysis

Halocarbocyclization Entry into the Oxabicyclo[4.3.1]decyl Exomethylene-δ-Lactone Cores of Linearifolin and Zaluzanin A: Exploiting Combinatorial Catalysis

Dialkylaluminum N,O-Dimethylhydroxylamine Complex as a Reagent to Mask Reactive Carbonyl Groups in Situ from Nucleophiles