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Structure of FD-895 revealed through total synthesis.

ABSTRACT: The total synthesis of FD-895 was completed through a strategy that featured the use of a tandem esterification ring-closing metathesis (RCM) process to construct the 12-membered macrolide and a modified Stille coupling to append the side chain. These studies combined with detailed analysis of all four possible C16-C17 stereoisomers were used to confirm the structure of FD-895 and identify an analog with an enhanced subnanomolar bioactivity.

SUBMITTER: Villa R

PROVIDER: S-EPMC3518397 | biostudies-literature | 2012 Nov

REPOSITORIES: biostudies-literature

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Structure of FD-895 revealed through total synthesis.

Villa Reymundo R Mandel Alexander L AL Jones Brian D BD La Clair James J JJ Burkart Michael D MD

Organic letters 20121016 21

The total synthesis of FD-895 was completed through a strategy that featured the use of a tandem esterification ring-closing metathesis (RCM) process to construct the 12-membered macrolide and a modified Stille coupling to append the side chain. These studies combined with detailed analysis of all four possible C16-C17 stereoisomers were used to confirm the structure of FD-895 and identify an analog with an enhanced subnanomolar bioactivity. ...[more]

PMID: 23072504

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