Studies toward the synthesis of vineomycinone B2 methyl ester

ORGN 160

Chi-Li Chen, chi-li@mail.utexas.edu and Stephen F. Martin, sfmartin@mail.utexas.edu. Department of Chemistry, University of Texas at Austin, 1 University Station A5300, Austin, TX 78712-0165
A new approach to the antibiotic C-aryl glycoside vineomycinone B2 methyl ester (5) is relied on the silicon tether as disposable linkers to control the regiochemistry of benzyne-furan cycloadditions for the construction of the aryl C-glycoside linkage. Diels-Alder precursor 1 was treated with n-BuLi to provide bisoxabenzonorbornadiene 2. After tether cleavage with KOH, followed by ring opening with hydrochloric acid and oxidation in the air, anthraquinone 3 was generated in moderate yields. Deprotecting of PMP group and oxidation of alcohol to the acid gave anthraquinone 4. The following stages of this approach included protecting acid with methyl group and deprotecting benzyl groups to give vineomycinone B2 methyl ester (5).

 

Asymmetric Reactions and Syntheses, Physical Organic Chemistry, Combinatorial Chemistry, Total Synthesis
8:00 PM-10:00 PM, Sunday, 26 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006