Formal Synthesis of (-)-Diazonamide A

C.-M. Cheung; F. W. Goldberg; P. Magnus; C. J. Russell; R. Turnbull; V. Lynch

doi:10.1055/s-2007-992499

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Synfacts 2008(2): 0117-0117
DOI: 10.1055/s-2007-992499

Synthesis of Natural Products and Potential Drugs

Formal Synthesis of (-)-Diazonamide A

Contributor(s): Philip Kocienski
C.-M. Cheung, F. W. Goldberg, P. Magnus*, C. J. Russell, R. Turnbull, V. Lynch
University of Texas at Austin, USA

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Publication History

Publication Date:
23 January 2008 (online)

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Significance

Diazonamide A, a metabolite of the ascidian Diazona angulata, displays potent in vitro activity against human colon cancer. A very easy O-aryl to C-aryl migration of O-tyrosine ethers B and C was used to generate the C10 quaternary stereogenic center in D and E.