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A Chemoenzymatic Total Synthesis of the Undecenolide (�)-Cladospolide B via a Mid-Stage Ring-Closing Metathesis and a Late-Stage Photo-Rearrangement of the E -Isomer

Jackson, Kerrie; Banwell, Martin; Loong, David; Rae, A David; Willis, Anthony


A sixteen-step synthesis of the twelve-membered macrolide (-)-cladospolide B (2) from the microbially-derived cis-1,2-dihydrocatechol 5 is described. Pivotal steps include the ring-closing metathesis (RCM) of diene 12 to give the ten-membered lactone 13 together with small amounts of the head-to-tail and head-to-head dimers 14 and 15, respectively. The saturated lactol 19 derived from compounds 13 and 14 readily participates in a Wadsworth-Horner-Emmons reaction to give the E-configured...[Show more]

CollectionsANU Research Publications
Date published: 2005
Type: Journal article
Source: Organic and Biomolecular Chemistry
DOI: 10.1039/b417685e


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