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Synfacts 2005(0): 0014-0014
DOI: 10.1055/s-2005-865352
DOI: 10.1055/s-2005-865352
Synthesis of Natural Products and Drugs
© Georg Thieme Verlag Stuttgart · New York
Total Synthesis of (+)-Myristinin A, a Potent DNA-Damaging Agent
Contributor(s): Philip Kocienski, Thomas SnaddonD. J. Maloney, J.-Z. Deng, S. R. Starck, Z. Gao, S. M. Hecht*
University of Virginia, Charlottesville, USA
(+)-Myristinin A, a Naturally Occurring DNA Polymerase β Inhibitor and Potent DNA Damaging Agent
J. Am. Chem. Soc. 2005, 127: 4140-4141
University of Virginia, Charlottesville, USA
(+)-Myristinin A, a Naturally Occurring DNA Polymerase β Inhibitor and Potent DNA Damaging Agent
J. Am. Chem. Soc. 2005, 127: 4140-4141
Further Information
Publication History
Publication Date:
20 July 2005 (online)
Key words
oxidation - -
Significance
Myristinin A is a flavanoid recently isolated from Myristica cinnamomea and Knema elegans. It displays DNA-damaging and polymerase β inhibitory activity. Hecht and co-workers provide details of the absolute stereochemistry of the natural product as well as biological studies related to its DNA-cleaving abilities.
Comment
The key step in this synthesis is the benzylic oxidation of B to generate C in excellent yield. Installation of this 4-O-alkylated moiety allows the Lewis acid-induced incorporation of D with excellent stereocontrol (>95:5) affording E.