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CC BY 4.0 · SynOpen 2022; 06(04): 312-318
DOI: 10.1055/s-0042-1751381
DOI: 10.1055/s-0042-1751381
paper
Stereoselective Synthesis of Euscapholide and Tetraketide via Prins Cyclisation and Ring-Closing Metathesis
Financial support was provided by the Council of Scientific and Industrial Research (CSIR), New Delhi.
Abstract
A concise and diastereoselective total synthesis of tetraketide and euscapholide is described in ten steps in 10.6% overall yield from acetaldehyde and (S)-pent-4-ene-1,2-diol. Jacobsen hydrolytic kinetic resolution, Prins cyclization, ring-closing metathesis and oxa-Michael addition reactions are the key steps involved in the synthesis.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751381.
- Supporting Information
Publication History
Received: 12 September 2022
Accepted after revision: 13 October 2022
Article published online:
24 November 2022
© 2022. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)
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For the Prins cyclization, see, for example: