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

Laksamee Jeanmard; Giacomo Lodovici; Ian George; Joshua T W Bray; Adrian C Whitwood; Gavin H Thomas; Ian J S Fairlamb; William P Unsworth; Paul A Clarke

doi:10.1039/d4cc01738b

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

Laksamee Jeanmard, Giacomo Lodovici, Ian George, Joshua T W Bray, Adrian C Whitwood, Gavin H Thomas, Ian J S Fairlamb, William P Unsworth, Paul A Clarke

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Number of pages	4
Journal	Chemical communications
Early online date	7 May 2024
DOIs	https://doi.org/10.1039/d4cc01738b https://doi.org/10.1039/d4cc01738b
Publication status	E-pub ahead of print - 7 May 2024

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10.1039/d4cc01738bLicence: CC BY
10.1039/d4cc01738b

d4cc01738b
© The Royal Society of Chemistry 2024
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Jeanmard, L., Lodovici, G., George, I., Bray, J. T. W., Whitwood, A. C., Thomas, G. H., Fairlamb, I. J. S., Unsworth, W. P., & Clarke, P. A. (2024). Stereoselective synthesis of an advanced trans-decalin intermediate towards the total synthesis of anthracimycin. Chemical communications. Advance online publication. https://doi.org/10.1039/d4cc01738b, https://doi.org/10.1039/d4cc01738b

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AU - Jeanmard, Laksamee

AU - Lodovici, Giacomo

AU - George, Ian

AU - Bray, Joshua T W

AU - Whitwood, Adrian C

AU - Thomas, Gavin H

AU - Fairlamb, Ian J S

AU - Unsworth, William P

AU - Clarke, Paul A

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AB - 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.

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

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