Chinese Journal of Organic Chemistry >
Efficient Construction of the Core Pentacyclic Skeleton of Communesin Alkaloids
Received date: 2024-08-06
Revised date: 2024-09-09
Online published: 2024-10-29
Supported by
National Natural Science Foundation of China(22301245); National Natural Science Foundation of China(22371231)
Communesin alkaloids are a family of complex dimeric cyclotryptamine alkaloids isolated from the marine fungi of the genus penicillium. These indole alkaloids contain a unique caged heptacyclic skeleton along with five stereogenic centers at least, two of which are the contiguous quaternary carbon centers (CQCCs), thus presenting remarkable synthetic challenges. Herein, an expedient construction core pentacyclic ring system of communesins is developed. The key steps include a catalytic asymmetric conjugated addition promoted by Ni(II)/chiral N,O-chiral dioxide for establishing the CQCCs and a deprotection/ring-opening reaction/cyclization cascade for setting up the pentacyclic skeleton.
Zhitong Yang , Hengqian Song , Pan Lei , Jiahang Yan , Weiqing Xie . Efficient Construction of the Core Pentacyclic Skeleton of Communesin Alkaloids[J]. Chinese Journal of Organic Chemistry, 2025 , 45(3) : 1003 -1008 . DOI: 10.6023/cjoc202408006
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