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Enantioselective Total Synthesis of the Osteoclastogenesis Inhibitor (+)‐Symbioimine
Author(s) -
Kim Justin,
Thomson Regan J.
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.200605160
Subject(s) - iminium , enantioselective synthesis , total synthesis , stereochemistry , intramolecular force , ring (chemistry) , stereocenter , alkaloid , chemistry , biology , biochemistry , catalysis , organic chemistry
No bones about it : The first enantioselective total synthesis of the osteoclastogenesis inhibitor (+)‐symbioimine ( 1 ) has been achieved. The synthesis features a convergent enol silane addition to a dimethyl acetal and a key, possibly biomimetic, intramolecular Diels–Alder reaction promoted by a dihydropyridinium ion to build four of the five requisite stereocenters in one step.