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Total Syntheses of Periconiasins A–E
Author(s) -
Tian Chong,
Lei Xiaoqiang,
Wang Yuanhao,
Dong Zhen,
Liu Gang,
Tang Yefeng
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.201602439
Subject(s) - tandem , polyketide , chemistry , stereochemistry , aldol condensation , total synthesis , aldol reaction , fragmentation (computing) , protonation , organic chemistry , computer science , materials science , catalysis , ion , operating system , biosynthesis , composite material , enzyme
The first and collective total syntheses of periconiasins A–E, a group of naturally occurring cytochalasans, were achieved by a series of rationally designed or bioinspired transformations. Salient features of the syntheses include a tandem aldol condensation/Grob fragmentation to assemble the linear polyketide–amino acid hybrid precursor, a Diels–Alder macrocylization to construct the 9/6/5 tricyclic core of periconiasins A–C, and a transannular carbonyl–ene reaction to forge the polycyclic framework of periconiasins D and E.