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Synthesis 2015; 47(01): 1-21
DOI: 10.1055/s-0034-1378676
DOI: 10.1055/s-0034-1378676
review
The Diels–Alder Reaction in Steroid Synthesis
Further Information
Publication History
Received: 11 August 2014
Accepted: 17 September 2014
Publication Date:
17 November 2014 (online)
Dedicated to Professor Lew Mander on the occasion of his 75th birthday
Abstract
This review explores the myriad ways in which the Diels–Alder reaction has been employed in the construction of the tetracyclic steroid nucleus. A systematic analysis of possible approaches highlights both the synthetic versatility of this ubiquitous reaction and also opportunities for new routes to fused tetracarbocyclic steroid frameworks.
1.1 Introduction
1.2 Classification of the Approaches
2.1 Installation of a Non-Skeletal Ring
2.2 Construction of the A-Ring
2.3 Construction of the B-Ring
2.4 Construction of the C-Ring
2.5 Double Diels–Alder Sequences
3 Conclusions and Future Prospects
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