Formal Total Synthesis of (+)-Citrafungin A

Sammi Tsegay; Helmut Hügel; Mark A. Rizzacasa

doi:10.1071/CH09182

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Formal Total Synthesis of (+)-Citrafungin A

Sammi Tsegay ^A , Helmut Hügel ^B and Mark A. Rizzacasa ^A ^C

+ Author Affiliations

- Author Affiliations

^A School of Chemistry, Bio21 Institute, University of Melbourne, Vic. 3010, Australia.

^B School of Applied Sciences [Applied Chemistry], RMIT University, Bowen Street, Melbourne, Vic. 3001, Australia.

^C Corresponding author. Email: masr@unimelb.edu.au

Australian Journal of Chemistry 62(7) 676-682 https://doi.org/10.1071/CH09182
Submitted: 1 April 2009 Accepted: 8 April 2009 Published: 13 July 2009

Abstract

The formal total synthesis of the fungal GGTase I inhibitor (+)-citrafungin A 1 is described. The key steps include a selective vinyl anion addition of the anion derived from iodide 10 to the lactone 9 and lactonization/selective deprotection of the allylic alcohols 8 and 23 to afford the citrafungin lactone. Esterification with the isocitrate 6 afforded citrafungin A tetra-t-butyl ester 5 which completed the formal total synthesis.

Acknowledgements

This research was funded by the ARC-Discovery Projects grant scheme. We are indebted to Dr Sheo B. Singh (Merck, Rahway, NJ) for the authentic sample of citrafungin A 1, and Professor Tony Barrett (Imperial College, UK) for providing us with a preprint of his paper.

References

Formal Total Synthesis of (+)-Citrafungin A

Abstract

Acknowledgements

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