You are here

J Org Chem DOI:10.1021/jo4000916

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

Publication TypeJournal Article
Year of Publication2013
AuthorsGerard, B, Lee, MD, Dandapani, S, Duvall, JR, Fitzgerald, ME, Kesavan, S, Lowe, JT, Marie, J-C, Pandya, BA, Suh, B-C, O'Shea, MWelzel, Dombrowski, M, Hamann, D, Lemercier, B, Murillo, T, Akella, LB, Foley, MA, Marcaurelle, LA
JournalJ Org Chem
Volume78
Issue11
Pages5160-71
Date Published2013 Jun 07
ISSN1520-6904
KeywordsGlycosides, Molecular Conformation, Pyrans, Stereoisomerism
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.

URLhttp://dx.doi.org/10.1021/jo4000916
DOI10.1021/jo4000916
Pubmed

http://www.ncbi.nlm.nih.gov/pubmed/23692141?dopt=Abstract

Alternate JournalJ. Org. Chem.
PubMed ID23692141
PubMed Central IDPMC3752688
Grant ListU54 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