Expedient Construction of the [5-6-7] Tricyclic Core of Calyciphylline A-Type Alkaloids

Expedient Construction of the [5-6-7] Tricyclic Core of Calyciphylline A-Type Alkaloids
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Calyciphylline A型生物碱[5-6-7]三环核心的便捷构建

DOI:
10.1002/asia.201403061
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发表时间:
2015-04-01
影响因子:
4.1
通讯作者:
Zhai, Hongbin
Zhai, Hongbin
中科院分区:
化学3区
文献类型:
--
作者:
Guo, Jing-Jing;Li, Yun;Zhai, Hongbin

文献摘要

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本文报道了一条合成高度稠合的[5-6-7]三环环的萼甲素A型生物碱的有效路线。这种方法的特点是一个高效的分子内Diels-Alder环加成,建立氮杂五元C环以及C1全碳季中心,和随后的环丙烷化与所得加合物的扩环反应一起构建七元D环。
An efficient synthetic route toward the highly congested [5-6-7] tricyclic core of calyciphylline A-type alkaloids has been developed. This approach features a highly efficient intramolecular Diels-Alder cycloaddition to establish the aza-five-membered C ring as well as the C1 all-carbon quaternary center, and a subsequent cyclopropanation together with a ring-expansion reaction of the resulted adduct to construct the seven-membered D ring.