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Studies toward the Synthesis of Azadirachtin, Part 1: Total Synthesis of a Fully Functionalized ABC Ring Framework and Coupling with a Norbornene Domain
Author(s) -
Nicolaou K. C.,
Sasmal Pradip K.,
Roecker A. J.,
Sun XiaoWen,
Mandal Sunil,
Converso Antonella
Publication year - 2005
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.200500216
Subject(s) - azadirachtin , decalin , norbornene , total synthesis , coupling (piping) , stereochemistry , ring (chemistry) , chemistry , combinatorial chemistry , organic chemistry , materials science , biology , catalysis , polymer , monomer , pesticide , agronomy , metallurgy
The advanced decalin intermediate 1 was synthesized and elaborated into the potential azadirachtin precursor 2 . The challenging synthesis involved several protecting‐group manipulations and coupling of 1 with an appropriate norbornene unit.