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Cascade Claisen Rearrangement: Rapid Synthesis of Polysubstituted Salicylaldehydes and Total Syntheses of Hemigossypol and Gossypol
Author(s) -
Cao Tongxiang,
Kong Yi,
Luo Kui,
Chen Lianfen,
Zhu Shifa
Publication year - 2018
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.201801612
Subject(s) - claisen rearrangement , chemistry , gossypol , total synthesis , propargyl , cascade , ether , catalysis , carroll rearrangement , combinatorial chemistry , organic chemistry , medicinal chemistry , biochemistry , chromatography
A cascade Claisen rearrangement of a well‐organized maltol propargyl ether for the construction of polysubstituted salicylaldehydes is reported. This reaction features high atom economy (100 %), as well as catalyst‐free and gram‐scale conditions. Based on this novel methodology, the total synthesis of hemigossypol, gossypol, and their analogues has been realized.