CC BY 4.0 · SynOpen 2022; 06(04): 312-318
DOI: 10.1055/s-0042-1751381
paper

Stereoselective Synthesis of Euscapholide and Tetraketide via Prins Cyclisation and Ring-Closing Metathesis

Dhanraj O. Biradar
a   Indian Institute of Chemical Technology, Hyderabad-500007, Telangana, India
b   Maharashtra Mahavidyalaya, Nilanga-413521, Dist. Latur, M.S, India
,
c   BSS Arts, Science & Commerce College, Makni, Tq. Lohara-413604, Dist. Osmanabad, M.S., India
,
Basi V. Subba Reddy
a   Indian Institute of Chemical Technology, Hyderabad-500007, Telangana, India
› Author Affiliations
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



Publication History

Received: 12 September 2022

Accepted after revision: 13 October 2022

Article published online:
24 November 2022

© 2022. 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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