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Chiral Dendralenes for Rapid Access to Enantiomerically Pure Polycycles
Author(s) -
Miller Natalie A.,
Willis Anthony C.,
PaddonRow Michael N.,
Sherburn Michael S.
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.200603335
Subject(s) - domino , ring (chemistry) , stereoselectivity , simple (philosophy) , stereochemistry , chemistry , scheme (mathematics) , computer science , combinatorial chemistry , catalysis , organic chemistry , mathematics , philosophy , mathematical analysis , epistemology
On a short fuse : Highly stereoselective and atom‐efficient domino Diels–Alder/lactonization/Diels–Alder sequences can be carried out using simple chiral [3]dendralenes to form fused‐ring systems. This short and general approach to cross‐conjugated systems promotes the rapid assembly of enantiomerically pure polycyclic ring systems common to biologically interesting terpenoids with virtually complete stereocontrol (see scheme).