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

J Org Chem
Authors
Baudouin Gerard
Maurice Lee
Sivaraman Dandapani
Jeremy Duvall
Mark Fitzgerald
Sarathy Kesavan
Jason Lowe
Jean-Charles Marie
Bhaumik Pandya
Byung-Chul Suh
Morgan O'Shea
Michael Dombrowski
Diane Hamann
Berenice Lemercier
Tiffanie Murillo
Lakshmi Akella
Michael Foley
Lisa Marcaurelle
Keywords
Stereoisomerism
Molecular Conformation
Pyrans
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.
Year of Publication
2013
Journal
J Org Chem
Volume
78
Issue
11
Pages
5160-71
Date Published
2013 Jun 07
ISSN
1520-6904
URL
http://dx.doi.org/10.1021/jo4000916
DOI
10.1021/jo4000916
PubMed ID
23692141
PubMed Central ID
PMC3752688
Links
Grant list
U54 RL1CA133834 / CA / NCI NIH HHS / United States
UL1DE019585 / DE / NIDCR NIH HHS / United States
RL1HG004671 / HG / NHGRI NIH HHS / United States
UL1 DE019585 / DE / NIDCR NIH HHS / United States
RL1GM084437 / GM / NIGMS NIH HHS / United States
P50 GM069721 / GM / NIGMS NIH HHS / United States
RL1 GM084437 / GM / NIGMS NIH HHS / United States
RL1 HG004671 / HG / NHGRI NIH HHS / United States
RL1 CA133834 / CA / NCI NIH HHS / United States

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