Enantioselective Total Synthesis of (-)-Salinosporamide A (NPI-0052)

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• 作者：Taotao Ling ; Venkat R. Macherla ; Rama Rao Manam ; Katherine A. McArthur ; Barbara C. M. Potts
• 刊名：Organic Letters
• 出版年：2007
• 出版时间：June 7, 2007
• 年：2007
• 卷：9
• 期：12
• 页码：2289 - 2292
• 全文大小：101K
• 年卷期：v.9,no.12(June 7, 2007)
• ISSN：1523-7052

文摘

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