Asymmetric Total Synthesis of Lancifodilactone G Acetate. 1. Diastereoselective Synthesis of CDEFGH Ring System

Asymmetric Total Synthesis of Lancifodilactone G Acetate. 1. Diastereoselective Synthesis of CDEFGH Ring System
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兰西福双内酯 G 乙酸酯的不对称全合成。

DOI:
10.1021/acs.joc.7b02915
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发表时间:
2018
影响因子:
3.6
通讯作者:
Yang Zhen
Yang Zhen
中科院分区:
化学2区
文献类型:
--
作者:
Sun Tian Wen;Liu Dong Dong;Wang Kuang Yu;Tong Bing Qi;Xie Jia Xin;Jiang Yan Long;Li Yong;Zhang Bo;Liu Yi Fan;Wang Yuan Xian;Zhang Jia Jun;Chen Jia Hua;Yang Zhen

文献摘要

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描述了Lancifodilactone G的CDEFGH环系统的立体选择性构建。该合成中的关键步骤是(i)用于形成氧杂桥连八元环的闭环复分解;(ii)用于构建空间拥挤F环的分子内Pauson-Khand反应;以及(iii)用于安装lancifodilactone G的端基异构体稳定的双螺缩酮片段的顺序交叉复分解、氢化和内酯化反应。
The stereoselective construction of the CDEFGH ring system of lancifodilactone G is described. The key steps in this synthesis are (i) ring-closing metathesis for formation of the oxa-bridged eight-membered ring; (ii) an intramolecular Pauson–Khand reaction for construction of the sterically congested F ring; and (iii) sequential cross-metathesis, hydrogenation, and lactonization reactions for installation of the anomerically stabilized bis-spiro ketal fragment of lancifodilactone G.