Enantioselective total synthesis of (-)-Salinosporamide A (NPI-0052).

نویسندگان

  • Taotao Ling
  • Venkat R Macherla
  • Rama Rao Manam
  • Katherine A McArthur
  • Barbara C M Potts
چکیده

A novel enantioselective total synthesis of 20S proteasome inhibitor Salinosporamide A (NPI-0052; 1) is presented. Key features include intramolecular aldol cyclization of 6 to simultaneously generate the three chiral centers of advanced intermediate 5, cyclohexene ring addition using B-2-cyclohexen-1-yl-9-BBN, and inversion of the C-5 stereocenter by oxidation followed by enantioselective enzymatic reduction.

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J. Antibiot. 60(1): 13–19, 2007

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عنوان ژورنال:
  • Organic letters

دوره 9 12  شماره 

صفحات  -

تاریخ انتشار 2007