TY - JOUR
T1 - The zipper-mode domino intramolecular Diels-Alder reaction
T2 - A new 0 → ABCD strategy for steroids and related compounds
AU - Nrret, Marck
AU - Sherburn, Michael S.
PY - 2001/11/5
Y1 - 2001/11/5
N2 - Four C-C bonds, four rings, and eight contiguous stereocenters in one go! Tetracyclic product 2, which results on warming simple acyclic precursor 1 with a mild Lewis acid, is formed through an efficient and highly stereoselective domino sequence of two intramolecular Diels-Alder reactions. Pharmacologically important norsteriods are just one potential application of this extremely effective approach to fused polycyclic systems.
AB - Four C-C bonds, four rings, and eight contiguous stereocenters in one go! Tetracyclic product 2, which results on warming simple acyclic precursor 1 with a mild Lewis acid, is formed through an efficient and highly stereoselective domino sequence of two intramolecular Diels-Alder reactions. Pharmacologically important norsteriods are just one potential application of this extremely effective approach to fused polycyclic systems.
KW - Cycloaddition
KW - Diastereoselectivity
KW - Domino reactions
KW - Polycycles
KW - Steriods
UR - http://www.scopus.com/inward/record.url?scp=0035813893&partnerID=8YFLogxK
U2 - 10.1002/1521-3773(20011105)40:21<4074::AID-ANIE4074>3.0.CO;2-J
DO - 10.1002/1521-3773(20011105)40:21<4074::AID-ANIE4074>3.0.CO;2-J
M3 - Article
SN - 1433-7851
VL - 40
SP - 4074
EP - 4076
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 21
ER -