A Chemoenzymatic Total Synthesis of the Undecenolide (−)-Cladospolide C

Martin G. Banwell; David T. J. Loong; Anthony C. Willis

doi:10.1071/CH05074

RESEARCH ARTICLE

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A Chemoenzymatic Total Synthesis of the Undecenolide (−)-Cladospolide C

Martin G. Banwell ^A ^B , David T. J. Loong ^A and Anthony C. Willis ^A

+ Author Affiliations

- Author Affiliations

^A Research School of Chemistry, Institute of Advanced Studies, Australian National University, Canberra ACT 0200, Australia.

^B Corresponding author. Email: mgb@rsc.anu.edu.au

Australian Journal of Chemistry 58(7) 511-516 https://doi.org/10.1071/CH05074
Submitted: 15 March 2005 Accepted: 4 May 2005 Published: 21 July 2005

Abstract

The (−)-enantiomer, ent-3, of the natural product (+)-cladospolide C (3) has been prepared for the first time using the monochiral cis-1,2-dihydrocatechol 5 as starting material. Key steps include coupling of the derived acid 6 with the enzymatically generated (S)-(+)-4-penten-2-ol (7) and ring-closing metathesis (RCM) of the resultant doubly unsaturated ester 8 to give lactone 9. The structure of this last compound has been confirmed by single-crystal X-ray analysis. This work has established that the absolute configuration of (+)-cladospolide C has been correctly assigned and is as illustrated in structure 3.

Acknowledgments

Dr Gregg Whited (Genencor International Inc., Palo Alto, CA) and Professor Tomas Hudlicky (Brock University) are warmly thanked for providing us with generous quantities of compound 5.

References

A Chemoenzymatic Total Synthesis of the Undecenolide (−)-Cladospolide C

Abstract

Acknowledgments

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