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Collective Total Synthesis of Aspidofractinine Alkaloids through the Development of a Bischler–Napieralski/Semipinacol Rearrangement Reaction
Author(s) -
Wang ShuangHu,
Si RuiQi,
Zhuang QingBo,
Guo Xiang,
Ke Tian,
Zhang XiaoMing,
Zhang FuMin,
Tu YongQiang
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202009238
Subject(s) - chemistry , heptane , ring (chemistry) , indole test , tandem , stereochemistry , total synthesis , combinatorial chemistry , medicinal chemistry , organic chemistry , materials science , composite material
A tandem Bischler–Napieralski/semipinacol rearrangement reaction has been developed for the purpose of assembling a bis(spirocyclic) indole framework, a privileged structural unit of aspidofractinine‐type monoterpenoid indole alkaloids, and was used in combination with a subsequent Mannich reaction to expeditiously construct the central bridged bicyclo[2.2.1]heptane ring system of these molecules with contiguous quaternary centers. The development of this novel strategy culminated in the collective total synthesis of four aspidofractinine alkaloids.