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Synfacts 2005(0): 0010-0010
DOI: 10.1055/s-2005-865347
DOI: 10.1055/s-2005-865347
Synthesis of Natural Products and Drugs
© Georg Thieme Verlag Stuttgart · New York
Asymmetric Zn Aldol Additions: Asymmetric Synthesis of Fostriecin
Contributor(s): Philip KocienskiB. M. Trost*, M. U. Frederiksen, J. P. N. Papillion, P. E. Harrington, S. Shin, B. T. Shireman
Stanford University, USA
Dinuclear Asymmetric Zn Aldol Additions: Formal Asymmetric Synthesis of Fostriecin
J. Am. Chem. Soc. 2005, 127: 3666-3667
Stanford University, USA
Dinuclear Asymmetric Zn Aldol Additions: Formal Asymmetric Synthesis of Fostriecin
J. Am. Chem. Soc. 2005, 127: 3666-3667
Further Information
Publication History
Publication Date:
20 July 2005 (online)
Key words
aldols - alkenylsilanes - cross-coupling
Significance
Fostriecin is a metabolite of Streptomyces pulveraceous. It is a potent inhibitor of protein phosphatase 2A and it is cytotoxic towards leukemia and many other cell lines.
Comment
The two markworthy steps in this short synthesis are (a) the large scale (49.6 mmol) direct asymmetric Zn-catalyzed aldol reaction illustrated and (b) a Pd-catalyzed alkenylsilane cross-coupling which installs the conjugated triene moiety. The synthesis was accomplished in 14 steps for the longest linear sequence and gave dephospho-fostriecin in 8.5% overall yield.