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Isolation and Asymmetric Total Synthesis of Perforanoid A
Author(s) -
Lv Chao,
Yan Xiaohui,
Tu Qian,
Di Yingtong,
Yuan Chunmao,
Fang Xin,
BenDavid Yaacove,
Xia Lei,
Gong Jianxian,
Shen Yuemao,
Yang Zhen,
Hao Xiaojiang
Publication year - 2016
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.201602783
Subject(s) - isolation (microbiology) , chemistry , biology , microbiology and biotechnology
A novel limonoid, perforanoid A, was isolated, and an asymmetric total synthesis was achieved in 10 steps. The key steps are chiral tertiary aminonaphthol mediated enantioselective alkenylation of an aldehyde to an allylic alcohol, Pd‐catalyzed coupling of the allylic alcohol with vinyl ether to form the γ‐lactone ring, and cyclopentenone ring formation through a Rh‐catalyzed Pauson–Khand reaction. Preliminary studies show that perforanoid A is cytotoxic towards HEL, K562, and CB3 tumor cell lines.