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有机金属对映体支架:有机金属手性子。通过钼介导的[5 + 2]环加成全合成(-)-包公藤A。

Organometallic enantiomeric scaffolding: organometallic chirons. Total synthesis of (-)-Bao Gong Teng A by a molybdenum-mediated [5 + 2] cycloaddition.

作者信息

Zhang Yongqiang, Liebeskind Lanny S

机构信息

Sanford S. Atwood Chemistry Center, Emory University, Atlanta, Georgia 30322, USA.

出版信息

J Am Chem Soc. 2006 Jan 18;128(2):465-72. doi: 10.1021/ja055623x.

DOI:10.1021/ja055623x
PMID:16402833
Abstract

Bao Gong Teng A, an optically active tropane alkaloid with hypotensive and miotic activity isolated from the Chinese herb Erycibe obtusifolia Benth, was synthesized by an "organometallic chiron" strategy in which single enantiomers of TpMo(CO)(2)(eta(3)-pyridinyl) complexes are produced in quantity and then elaborated easily and efficiently to generate, after demetalation, highly enantiopure advanced synthetic intermediates possessing the tropane core.

摘要

包公藤甲素是从中药丁公藤中分离得到的一种具有降压和缩瞳活性的旋光性托烷生物碱,它通过一种“有机金属手性试剂”策略合成,其中大量制备了TpMo(CO)(2)(η(3)-吡啶基)配合物的单一对映体,然后经过脱金属作用,轻松高效地将其转化为具有托烷核心的高对映体纯的高级合成中间体。

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