A short sequence for the iterative synthesis of fused polyethers

Elustondo, F., Chintalapudi, V. and Clark, J. S. (2019) A short sequence for the iterative synthesis of fused polyethers. Helvetica Chimica Acta, 102(9), e1900161. (doi: 10.1002/hlca.201900161)

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A simple and efficient four‐step sequence for the synthesis of fused polyether arrays has been developed. Cyclic ethers are installed by sequential alkynyl ether formation, carbocupration, ring‐closing metathesis and hydroboration with acidic workup. Crucially, the alkene required for the subsequent ring formation by ring‐closing metathesis is present in the substrate but is masked in the form of a vinylic silane, which prevents competitive metathesis of the side chain. Generation of the reactive alkene from the unreactive vinylic silane is accomplished by hydroboration and subsequent acid‐mediated Peterson elimination of the intermediate hydroxysilane.

Item Type:Articles
Glasgow Author(s) Enlighten ID:Clark, Professor Stephen and Chintalapudi, Dr Rer Nat Venkaiah
Authors: Elustondo, F., Chintalapudi, V., and Clark, J. S.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Helvetica Chimica Acta
ISSN (Online):1522-2675
Published Online:26 August 2019
Copyright Holders:Copyright © 2019 The Authors
First Published:First published in Helvetica Chimica Acta 102(9):e1900161
Publisher Policy:Reproduced under a Creative Commons License

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
3024330Convergent Bidirectional Total Synthesis of Ciguatoxin CTX3CStephen ClarkEngineering and Physical Sciences Research Council (EPSRC)EP/R035423/1Chemistry