Journal article

Total Synthesis of Viridiofungins A and B

Liselle Atkin, Angus Robertson, Jonathan M White, Mark A Rizzacasa

ORGANIC LETTERS | AMER CHEMICAL SOC | Published : 2021

Abstract

The total synthesis of viridiofungins A (1) and B (2) via β-lactone 3 in 13 steps is reported. Key steps included an HF-mediated rearrangement of cyclobutene diester 9 to form a bicyclic lactone 6, an olefin cross metathesis between disubstituted alkene 3 and alkene 4 in which isomerization was suppressed, and a novel β-lactone ring opening to form the amide. Deprotection then gave either viridiofungin A (1) or B (2) in high yield.

Grants

Awarded by Australian Research Council Discovery Program


Funding Acknowledgements

We thank the Australian Research Council Discovery Program (DP200100722) and the University of Melbourne Faculty of Science Research Grant Support Scheme for funding. We also thank Dr. Christian Gunawan and Tony Duncan (Circa Pty Ltd.) for the generous gift of (S)-(+)-.-hydroxymethyl-.butyrolactone.