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Total synthesis of antibiotic C104: Benzyne-Furan cycloaddition approach to the angucyclines

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
51
Issue
27
Identifiers
DOI: 10.1016/0040-4020(95)00384-k

Abstract

Abstract First total synthesis of antibiotic C104 ( 1), a prototypical member of the angucyclines, was accomplished. Highly regioselective cycloaddition of α-alkoxybenzyne 12 with angularly fused α- siloxyfuran 10 enabled the straightforward construction of the characteristic benz[ a]anthraquinone framework. The D-olivosyl C-glycoside was introduced via the O → C-glycoside rearrangement in a regio- and stereoselective manner.

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