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Synfacts 2007(10): 1015-1015  
DOI: 10.1055/s-2007-968952
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (-)-Salinosporamide A

Contributor(s): Philip Kocienski, Stewart Eccles
T. Ling, V. R. Macherla*, R. R. Manam, K. A. McArthur, B. C. M. Potts
Nereus Pharmaceuticals, San Diego, USA
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Publication History

Publication Date:
07 November 2007 (online)

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Significance

Clinical trials are underway on salinosporamide for the treatment of cancer as it inhibits the 20S proteasome. An intramolecular aldol reaction converts A into intermediate D (100 g scale) with the simultaneous creation of three stereo­genic centers using Seebach’s self-regeneration of stereogenic centers strategy (D. Seebach, A. R. Sting, M. Hoffmann Angew. Chem. Int. Ed. 1996, 35, 2708).