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Synthetic Study Towards Azadirachtin: An Efficient and Stereoselective Construction of the AB Rings with Full Functionality
Author(s) -
Watanabe Hidenori,
Mori Naoki,
Itoh Daisuke,
Kitahara Takeshi,
Mori Kenji
Publication year - 2007
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.200604097
Subject(s) - azadirachtin , moiety , stereoselectivity , decarboxylation , intramolecular force , claisen rearrangement , chemistry , stereochemistry , decalin , ring (chemistry) , tandem , radical cyclization , combinatorial chemistry , organic chemistry , materials science , biology , pesticide , agronomy , composite material , catalysis
From A to B : The decalin moiety of azadirachtin, which includes the fully functionalized AB ring system (see picture), was synthesized stereoselectively in only 23 steps. Key steps include an intramolecular Diels–Alder reaction, a decarboxylation, a Claisen rearrangement, and finally a tandem radical cyclization.