The Zipper-Mode Domino Intramolecular Diels-Alder Reaction: A New 0→ABCD Strategy for Steroids and Related Compounds

Marck Nörret, Michael S Sherburn

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)4074-4076
Number of pages3
JournalAngewandte Chemie - International Edition
Volume40
Issue number21
DOIs
Publication statusPublished - 5 Nov 2001
Externally publishedYes

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