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Synfacts 2007(12): 1229-1229  
DOI: 10.1055/s-2007-991303
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Thapsigargin

Contributor(s): Philip Kocienski
S. P. Andrews, M. Ball, F. Wierschem, E. Cleator, S. Oliver, K. Högenauer, O. Simic, A. Antonello, U. Hünger, M. D. Smith, S. V. Ley*
Cambridge University, UK
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Publication History

Publication Date:
22 November 2007 (online)

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Significance

Thapsigargin is a potent inhibitor of sarco/endoplasmic reticulum ATPase (SERCA). By altering cellular Ca2+ levels, it disrupts cell growth and function. Peptide conjugates of thapsigargin have potential for the treatment of prostate cancer. The Cambridge synthesis (42 steps, 0.61% overall yield), starting from (S)-carvone, features an early Favorskii ring contraction to generate the cyclopentane B.