New and general a-selective glycosylation protocols for 2-deoxysugars, specifically developed for L-mycarose and L-kedarosamine

ORGN 585

Martin J. Lear, Isao Ohashi, Fumihiko Yoshimura, Yasuhito Koyama, and Masahiro Hirama. Department of Chemistry, Tohoku University, Graduade School of Science, Aza Aramaki, Sendai 980 8578, Japan
Direct, mild, and a-selective, glycosylation protocols for 2-deoxysugars developed for the total synthesis of the kedarcidin chromophore (ked-chr) will be systematically presented. Besides disclosure of concise synthetic procedures to 2-deoxypyranosides, specific developments include: (1) the general use of polystyrene-supported DBU to synthesize unstable Schmidt donors, (2) the general use of silver(I) salts to efficiently activate 2-deoxy sugars, and (3) the a-glycosylation of ansamacrolide and aglycon frameworks of the kedarcidin chromophore for both L-mycarose and L-kedarosamine. Notwithstanding discussion of mechanism and generality to 2-deoxysugar chemistry, application thereof and implementation in the total synthesis of ked-chr will be presented.

 

New Reactions, Methodology, Heterocycles, Aromatics
8:00 PM-10:00 PM, Wednesday, August 25, 2004 Pennsylvania Convention Center -- Hall D, Poster

Division of Organic Chemistry

The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004