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Synthesis of the cytotrienin A core via metal catalyzed C-C coupling.

ABSTRACT: A synthetic approach to the C17-benzene ansamycins via metal catalyzed C-C coupling is described. Key bond formations include direct iridium catalyzed carbonyl crotylation from the alcohol oxidation level followed by chelation-controlled Sakurai-Seyferth dienylation to form the stereotriad, which is attached to the arene via Suzuki cross-coupling. The diene-containing carboxylic acid is prepared using rhodium catalyzed acetylene-aldehyde reductive C-C coupling mediated by gaseous hydrogen. Finally, ring-closing metathesis delivers the cytotrienin core.

SUBMITTER: Rossle M

PROVIDER: S-EPMC3075014 | biostudies-literature | 2011 Mar

REPOSITORIES: biostudies-literature

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Synthesis of the cytotrienin A core via metal catalyzed C-C coupling.

Rössle Michael M Del Valle David J DJ Krische Michael J MJ

Organic letters 20110216 6

A synthetic approach to the C17-benzene ansamycins via metal catalyzed C-C coupling is described. Key bond formations include direct iridium catalyzed carbonyl crotylation from the alcohol oxidation level followed by chelation-controlled Sakurai-Seyferth dienylation to form the stereotriad, which is attached to the arene via Suzuki cross-coupling. The diene-containing carboxylic acid is prepared using rhodium catalyzed acetylene-aldehyde reductive C-C coupling mediated by gaseous hydrogen. Final ...[more]

PMID: 21323372

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