Premium
The Zipper‐Mode Domino Intramolecular Diels–Alder Reaction: A New 0→ABCD Strategy for Steroids and Related Compounds
Author(s) -
Nörret Marck,
Sherburn Michael S.
Publication year - 2001
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 - 10.1002/1521-3773(20011105)40:21<4074::aid-anie4074>3.0.co;2-j
Subject(s) - intramolecular force , stereocenter , domino , chemistry , stereochemistry , retrosynthetic analysis , stereoselectivity , sequence (biology) , combinatorial chemistry , total synthesis , enantioselective synthesis , organic chemistry , catalysis , biochemistry
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 norsteroids are just one potential application of this extremely effective approach to fused polycyclic systems.