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Synlett 2014; 25(1): 12-32
DOI: 10.1055/s-0033-1340073
DOI: 10.1055/s-0033-1340073
account
Strategies for the Synthesis of Cyclic Ethers of Marine Natural Products
Weitere Informationen
Publikationsverlauf
Received: 31. Juli 2013
Accepted after revision: 24. September 2013
Publikationsdatum:
26. November 2013 (online)
Abstract
This account describes our studies on the synthesis of natural products that contain cyclic ethers in their structures. An overview of the main methodologies is presented and several total syntheses developed by the group are described. We also discuss new applications based on the use of Prins and Nicolas reactions as key steps in the preparation of oxygenated heterocyclic compounds.
1 Introduction
1.1 Natural Sources and Biogenesis
2 Carbon–Oxygen Bond-Formation Approach
2.1 Intramolecular Opening of Epoxy Alcohols and Related Bromo Cyclizations
2.2 Intramolecular Hetero-Michael Reaction of Alkoxy γ-Benzoyloxy α,β-Unsaturated Esters
2.3 Intramolecular Nicholas Reaction
3 Ring-Closing Metathesis of Unsaturated Linear Ethers
4 Prins Cyclization Promoted by Iron(III) salts
4.1 General Strategy
4.2 Cyclization Using Alkynols and the Formation of Vinyl Halides
4.3 The Use of Trimethylsilyl and Electron-Withdrawing Substituents in the Synthesis of 2,6-Disubstituted Tetrahydropyrans
4.4 Catalytic Prins Cyclization
4.5 Synthesis of Oxepanes
5 Summary
-
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For preliminary results, see: