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Rapid Access to the “in,out”‐Tetracyclic Core of Ingenol
Author(s) -
Epstein Oleg L.,
Cha Jin Kun
Publication year - 2004
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.200461807
Subject(s) - core (optical fiber) , pinacol , alcohol , chemistry , stereochemistry , computer science , organic chemistry , telecommunications , catalysis
In … out … shake it all about! The tetracyclic core of ingenol has been prepared in a convergent synthesis. The pinacol‐type rearrangement of an epoxy alcohol provides a simple, expedient solution to the challenging “inside–outside” intrabridgehead stereochemistry of ingenol (see scheme, TBS= tert ‐butyldimethylsilyl).