The Journal of Organic Chemistry

Benzo [d] naphtho [1, 2-b] pyran-6-one C-glycosides. Aryltri-n-butylstannanes in palladium-mediated coupling with 2, 3-dihydropyran and furanoid glycals

RA Outten, GD Daves Jr

Index: Outten, Robert A.; Daves, G. Doyle Journal of Organic Chemistry, 1989 , vol. 54, # 1 p. 29 - 35

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Citation Number: 47

Abstract

Synthesis of benzo [d] naphtho [1, 2-b] pyran-6-one furanoid C-glycosides, related to the gilvocarcin, ravidomycin, and chrysomycin class of antibiotics, has been accomplished by regio-and stereospecific coupling of a furanoid glycal, 1, 4-anhydro-2-deoxy-5-0- (methoxymethyl)-3-0-[tris (l-methylethyl) silyl]-~-erythro-pent-l-enitol with tri-n-butylstannyl derivatives of benzo [d] naphtho [1,241 pyran-6-0nes in the presence of stoichiometric ...

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