The zipper-mode domino intramolecular Diels-Alder reaction: A new 0 → ABCD strategy for steroids and related compounds

Marck Nrret; Michael S. Sherburn

doi:10.1002/1521-3773(20011105)40:21<4074::AID-ANIE4074>3.0.CO;2-J

The zipper-mode domino intramolecular Diels-Alder reaction: A new 0 → ABCD strategy for steroids and related compounds

Marck Nrret
, Michael S. Sherburn^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-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 norsteriods are just one potential application of this extremely effective approach to fused polycyclic systems.

Original language	English
Pages (from-to)	4074-4076
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	40
Issue number	21
DOIs	https://doi.org/10.1002/1521-3773(20011105)40:21<4074::AID-ANIE4074>3.0.CO;2-J
Publication status	Published - 5 Nov 2001
Externally published	Yes

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KW - Cycloaddition

KW - Diastereoselectivity

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KW - Polycycles

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The zipper-mode domino intramolecular Diels-Alder reaction: A new 0 → ABCD strategy for steroids and related compounds

Abstract

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