The cyclobutene diester approach to alkyl citrate natural products

Nikolai P. Rossouw; Mark A. Rizzacasa

doi:10.1071/CH24088

REVIEW (Open Access)

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The cyclobutene diester approach to alkyl citrate natural products

Nikolai P. Rossouw ^A and Mark A. Rizzacasa

^A ^*

+ Author Affiliations

- Author Affiliations

^A School of Chemistry, The Bio21 Molecular Science and Biotechnology Institute, The University of Melbourne, Parkville, Vic. 3010, Australia.

^* Correspondence to: masr@unimelb.edu.au

Handling Editor: Curt Wentrup

Australian Journal of Chemistry 77, CH24088 https://doi.org/10.1071/CH24088

Submitted: 3 July 2024 Accepted: 24 July 2024 Published online: 22 August 2024

© 2024 The Author(s) (or their employer(s)). Published by CSIRO Publishing. This is an open access article distributed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License (CC BY-NC-ND)

Abstract

This review outlines the synthesis of alkyl citrate natural products using cyclobutene diester precursors. The approach is efficient and stereoselective and provides the correct oxidation state of the citrate core of these compounds. The synthesis of a number of alkyl citrates along with some higher oxidised members of this family is detailed.

Keywords: alkyl citrates, cyclobutenes, natural products, oxidation, rearrangement, total synthesis.

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