Synthesis of Anti-Angiogenic Isocoumarins

Author(s): Haiqing Yuan, Bernd Junker, Paul Helquist, Richard E. Taylor

Journal Name: Current Organic Synthesis

Volume 1 , Issue 1 , 2004

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A concise synthetic route has been developed for the preparation of the naturally occurring isocoumarin cytogenin and NM-3, an analogue with anti-angiogenic activity. The route is general and also provided C(3) side chain modified analogues. Key aspects of the synthesis include orthogonal protection of the two aromatic alkoxy groups, benzylic lithiation and carboxylation, use of the resulting carboxylic acid in a DCC-promoted acylation of Meldrums acid, and facile ester enolate alkylations for introduction of side chains for convenient generation of a new set of NM-3 analogues.

Keywords: anti-angiogenic, cytogenin, benzylic lithiation, ester enolate alkylation, isocoumarins, NM-3

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Article Details

Year: 2004
Page: [1 - 9]
Pages: 9
DOI: 10.2174/1570179043485411

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