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de novo asymmetric synthesis of daumone via a palladium-catalyzed glycosylation.
Org Lett. 2005 Sep 01; 7(18):3921-4.OL

Abstract

The enantioselective syntheses of daumone and two analogues have been achieved in seven to eight steps. This route relies upon a diasteroselective palladium-catalyzed glycosylation reaction for the formation of the anomeric bond. The asymmetry of the sugar and aglycone portion of daumone were introduced by Noyori reduction of an acylfuran and a propargyl ketone. A highly diastereoselective epoxidation and reductive ring opening established the desired C-2 and C-4 stereochemistry of daumone. [reaction: see text]

Authors+Show Affiliations

Department of Chemistry, West Virginia University, Morgantown, WV 26506, USA.No affiliation info available

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

16119932

Citation

Guo, Haibing, and George A. O'doherty. "De Novo Asymmetric Synthesis of Daumone Via a Palladium-catalyzed Glycosylation." Organic Letters, vol. 7, no. 18, 2005, pp. 3921-4.
Guo H, O'doherty GA. De novo asymmetric synthesis of daumone via a palladium-catalyzed glycosylation. Org Lett. 2005;7(18):3921-4.
Guo, H., & O'doherty, G. A. (2005). De novo asymmetric synthesis of daumone via a palladium-catalyzed glycosylation. Organic Letters, 7(18), 3921-4.
Guo H, O'doherty GA. De Novo Asymmetric Synthesis of Daumone Via a Palladium-catalyzed Glycosylation. Org Lett. 2005 Sep 1;7(18):3921-4. PubMed PMID: 16119932.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - de novo asymmetric synthesis of daumone via a palladium-catalyzed glycosylation. AU - Guo,Haibing, AU - O'doherty,George A, PY - 2005/8/27/pubmed PY - 2006/7/21/medline PY - 2005/8/27/entrez SP - 3921 EP - 4 JF - Organic letters JO - Org. Lett. VL - 7 IS - 18 N2 - The enantioselective syntheses of daumone and two analogues have been achieved in seven to eight steps. This route relies upon a diasteroselective palladium-catalyzed glycosylation reaction for the formation of the anomeric bond. The asymmetry of the sugar and aglycone portion of daumone were introduced by Noyori reduction of an acylfuran and a propargyl ketone. A highly diastereoselective epoxidation and reductive ring opening established the desired C-2 and C-4 stereochemistry of daumone. [reaction: see text] SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/16119932/de_novo_asymmetric_synthesis_of_daumone_via_a_palladium_catalyzed_glycosylation_ L2 - https://dx.doi.org/10.1021/ol051383e DB - PRIME DP - Unbound Medicine ER -