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Synfacts 2006(2): 0099-0099  
DOI: 10.1055/s-2005-921775
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of clastro-Lactacystin β-Lactone

Contributor(s): Philip Kocienski, John Cooksey
T. J. Donohoe*, H. O. Sintim, L. Sisangia, K. W. Ace, P. M. Guyo, A. Cowley, J. D. Harling
University of Oxford, UK
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Publication History

Publication Date:
23 January 2006 (online)

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Significance

The highlight in this total synthesis of clastro-lactacystin β-lactone is the anti-selective reductive aldol reaction of electron-deficient pyrrole A under ammonia-free Birch reduction conditions to construct key intermediate C. The Donohoe group has applied this methodology to the synthesis of other natural products including Nemorensic acid (T. J. Donohoe, J.-B. Guillermin, D. S. Walter J. Chem. Soc., Perkin Trans. 1 2002, 1369-1375) and Secosyrin 1 (T. J. Donohoe, H. O. Sintim Org. Lett. 2004, 6, 2003-2006).