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Synthesis of stereochemically and skeletally diverse fused ring systems from functionalized C-glycosides.

ABSTRACT: A diversity-oriented synthesis (DOS) strategy was developed for the synthesis of stereochemically diverse fused-ring systems containing a pyran moiety. Each scaffold contains an amine and methyl ester for further diversification via amine capping and amide coupling. Scaffold diversity was evaluated in comparison to previously prepared scaffolds by a shape-based principal moments of inertia (PMI) analysis.

SUBMITTER: Gerard B

PROVIDER: S-EPMC3752688 | biostudies-literature | 2013 Jun

REPOSITORIES: biostudies-literature

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Synthesis of stereochemically and skeletally diverse fused ring systems from functionalized C-glycosides.

Gerard Baudouin B Lee Maurice D MD Dandapani Sivaraman S Duvall Jeremy R JR Fitzgerald Mark E ME Kesavan Sarathy S Lowe Jason T JT Marié Jean-Charles JC Pandya Bhaumik A BA Suh Byung-Chul BC O'Shea Morgan Welzel MW Dombrowski Michael M Hamann Diane D Lemercier Berenice B Murillo Tiffanie T Akella Lakshmi B LB Foley Michael A MA Marcaurelle Lisa A LA

The Journal of organic chemistry 20130521 11

A diversity-oriented synthesis (DOS) strategy was developed for the synthesis of stereochemically diverse fused-ring systems containing a pyran moiety. Each scaffold contains an amine and methyl ester for further diversification via amine capping and amide coupling. Scaffold diversity was evaluated in comparison to previously prepared scaffolds by a shape-based principal moments of inertia (PMI) analysis. ...[more]

PMID: 23692141

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