Premium
Sterically Controlled Diels–Alder Cycloadditions: Rapid Entry into the Illudin Scaffold
Author(s) -
StevensCullinane Lars,
Lucas Nigel T.,
Hawkins Bill C.
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402461
Subject(s) - chemistry , cycloaddition , regioselectivity , steric effects , stereoselectivity , ring (chemistry) , tricyclic , diels–alder reaction , stereochemistry , organic chemistry , catalysis
Rapid entry into the tricyclic ring system of the illudin family of natural products was achieved using a Diels–Alder cycloaddition of allylidenecyclopropane 7 and various cyclic and acyclic dienophiles. The reaction proceeds with complete regioselectivity and moderate to high stereoselectivity in good to excellent chemical yields.