Synthesis of Stereochemically and Skeletally Diverse Fused Ring Systems from Functionalized C‑Glycosides

Synthesis of Stereochemically and Skeletally Diverse Fused Ring Systems from Functionalized C‑Glycosides

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...

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Veröffentlicht in:Journal of organic chemistry 2013-06, Vol.78 (11), p.5160-5171
Hauptverfasser: Gerard, Baudouin, Lee, Maurice D, Dandapani, Sivaraman, Duvall, Jeremy R, Fitzgerald, Mark E, Kesavan, Sarathy, Lowe, Jason T, Marié, Jean-Charles, Pandya, Bhaumik A, Suh, Byung-Chul, O’Shea, Morgan Welzel, Dombrowski, Michael, Hamann, Diane, Lemercier, Berenice, Murillo, Tiffanie, Akella, Lakshmi B, Foley, Michael A, Marcaurelle, Lisa A
Format: Artikel
Sprache:eng
Schlagworte:
Glycosides - chemical synthesis
Glycosides - chemistry
moieties
Molecular Conformation
organic chemistry
Pyrans - chemistry
stereochemistry
Stereoisomerism
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/jo4000916