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Synthesis 2024; 56(14): 2239-2246
DOI: 10.1055/s-0042-1751567
DOI: 10.1055/s-0042-1751567
paper
Synthesis of the Cyclohexane Fragment Peculiar to Enacyloxins: Study of Its Assembly and Protective Groups Removal
This work was funded by the Centre National de la Recherche Scientifique (CNRS) and the Université Paris Cité.
Abstract
The enantioselective synthesis of the protected (1S,3R,4S)-3,4-dihydroxycyclohexane-1-carboxylic acid moiety shared among all members of the enacyloxin family has been successfully accomplished. Having obtained this fragment, we devised assembly conditions using models that mimic the enacyloxin acyl chain. Additionally, we assessed conditions for the removal of protective groups, aiming to avoid previously reported detrimental ester shifts.
Key words
total synthesis - natural products - ring-closing metathesis - palladium - carbonylation - kinetic reprotonationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751567.
- Supporting Information
Publication History
Received: 23 January 2024
Accepted after revision: 15 February 2024
Article published online:
01 March 2024
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