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A chemoenzymatic total synthesis of the undecenolide (-)-cladospolide C

Banwell, Martin; Loong, David; Willis, Anthony

Description

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...[Show more]

CollectionsANU Research Publications
Date published: 2005
Type: Journal article
URI: http://hdl.handle.net/1885/81727
Source: Australian Journal of Chemistry
DOI: 10.1071/CH05074

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