Studies Toward the Total Synthesis and Stereochemical Assignment of Microspinosamide

Gajan Santhakumar; Richard J. Payne

doi:10.1071/CH15468

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Studies Toward the Total Synthesis and Stereochemical Assignment of Microspinosamide

Gajan Santhakumar ^A and Richard J. Payne ^A ^B

+ Author Affiliations

- Author Affiliations

^A School of Chemistry, The University of Sydney, Sydney, NSW 2006, Australia.

^B Corresponding author. Email: richard.payne@sydney.edu.au

Australian Journal of Chemistry 68(12) 1885-1889 https://doi.org/10.1071/CH15468
Submitted: 2 August 2015 Accepted: 8 September 2015 Published: 21 October 2015

Abstract

Efforts toward the total synthesis and stereochemical assignment of the cyclic depsipeptide natural product microspinosamide are described. A single diastereoisomer was targeted corresponding to the predicted structure of the natural product incorporating a (2S, 3R)-β-hydroxy-p-bromophenylalanine residue. Assembly was achieved through the initial synthesis of a cyclic depsipeptide and a linear peptide thioester fragment by solid-phase peptide synthesis, followed by fusion of the two fragments through a native chemical ligation–oxidation protocol. Extensive spectroscopic analysis showed structural differences to the isolated natural product, suggesting that a diastereoisomer of microspinosamide had been synthesised. This work lays the foundation for the future synthesis of the correct diastereoisomer.

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Studies Toward the Total Synthesis and Stereochemical Assignment of Microspinosamide

Abstract

References

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