Stereoselective synthesis of an advanced trans-decalin intermediate towards the total synthesis of anthracimycin

Abstract

Progress towards the total synthesis of the macrolide natural product anthracimycin is described. This new approach utilises an intermolecular Diels-Alder strategy followed by epimeirsation to form the key trans-decalin framework. The route culminates in the stereoselective synthesis of an advanced tricyclic lactone intermediate, containing five contiguous sterogenic centres with the correct relative and absolute stereochemistry required for the anthracimycin core motif.

Metadata

Item Type:	Article
Authors/Creators:	Jeanmard, Laksamee Lodovici, Giacomo George, Ian (ig602@york.ac.uk) Bray, Joshua T W https://orcid.org/0000-0003-2384-9675 Whitwood, Adrian C Thomas, Gavin H https://orcid.org/0000-0002-9763-1313 Fairlamb, Ian J S https://orcid.org/0000-0002-7555-2761 Unsworth, William P https://orcid.org/0000-0002-9169-5156 Clarke, Paul A https://orcid.org/0000-0003-3952-359X
Copyright, Publisher and Additional Information:	© The Royal Society of Chemistry 2024
Dates:	Published (online): 7 May 2024 Accepted: 3 May 2024
Institution:	The University of York
Academic Units:	The University of York > Faculty of Sciences (York) > Chemistry (York) The University of York > Faculty of Sciences (York) > Biology (York)
Depositing User:	Pure (York)
Date Deposited:	22 May 2024 08:20
Last Modified:	21 Jan 2025 18:13
Published Version:	https://doi.org/10.1039/d4cc01738b
Status:	Published online
Refereed:	Yes
Identification Number:	10.1039/d4cc01738b
Related URLs:	http://www.scopus.com/inward/record.url?...
Open Archives Initiative ID (OAI ID):	oai:eprints.whiterose.ac.uk:212592

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Stereoselective synthesis of an advanced trans-decalin intermediate towards the total synthesis of anthracimycin

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