Synthetic Study Towards Azadirachtin: An Efficient and Stereoselective Construction of the AB Rings with Full Functionality | Zendy

Watanabe Hidenori | Zendy; Mori Naoki | Zendy; Itoh Daisuke | Zendy; Kitahara Takeshi | Zendy; Mori Kenji | Zendy

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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.

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