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Expedient Construction of the [5‐6‐7] Tricyclic Core of Calyciphylline A‐Type Alkaloids
Author(s) -
Guo JingJing,
Li Yun,
Cheng Bin,
Xu Tingting,
Tao Cheng,
Yang Xinkan,
Zhang Denghong,
Yan Guangqi,
Zhai Hongbin
Publication year - 2015
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201403061
Subject(s) - intramolecular force , tricyclic , ring (chemistry) , cycloaddition , adduct , cyclopropanation , chemistry , stereochemistry , core (optical fiber) , quaternary carbon , organic chemistry , enantioselective synthesis , catalysis , materials science , composite material
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.
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