Total Synthesis of Fawcettimine-Type Alkaloid, Lycojaponicumin A

The efficient total synthesis of lycojaponicumin A (1) has been accomplished for the first time. The remarkable features of this novel strategy include the following: (1) rapid construction of tricyclic intermediate 4 through a regio- and stereoselective semipinacol ring expansion, which simplified...

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Bibliographic Details
Published in:Organic letters 2020-05, Vol.22 (10), p.3775-3779
Main Authors: Shao, Hui, Fang, Kun, Wang, Yun-Peng, Zhang, Xiao-Ming, Ding, Tong-Mei, Zhang, Shu-Yu, Chen, Zhi-Min, Tu, Yong-Qiang
Format: Article
Language:English
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Summary:The efficient total synthesis of lycojaponicumin A (1) has been accomplished for the first time. The remarkable features of this novel strategy include the following: (1) rapid construction of tricyclic intermediate 4 through a regio- and stereoselective semipinacol ring expansion, which simplified the construction of rings A and B of 1; (2) the subsequent regio- and stereoselective formation of the highly strained rings C–E of 1 through a tandem oxa-hetero [3 + 2] cycloaddition/N-cycloalkylation.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c00961