TOTAL SYNTHESIS OF ANTIBIOTIC C104 - BENZYNE-FURAN CYCLOADDITION APPROACH TO THE ANGUCYCLINES

Authors
MATSUMOTO T SOHMA T YAMAGUCHI H KURATA S SUZUKI K
Citation
T. Matsumoto et al., TOTAL SYNTHESIS OF ANTIBIOTIC C104 - BENZYNE-FURAN CYCLOADDITION APPROACH TO THE ANGUCYCLINES, Tetrahedron, 51(27), 1995, pp. 7347-7360
Citations number
46
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
27
Year of publication
1995
Pages
7347 - 7360
Database
ISI
SICI code
0040-4020(1995)51:27<7347:TSOAC->2.0.ZU;2-R
Abstract
First total synthesis of antibiotic C104 (1), a prototypical member of the angucyclines, was accomplished. Highly regioselective cycloadditi on of alpha-alkoxybenzyne 12 with angularly fused alpha-siloxyfuran 10 enabled the straightforward construction of the characteristic benz[a ]anthraquinone framework. The D-olivosyl C-glycoside was introduced vi a the O-->C-glycoside rearrangement in a regio- and stereoselective ma nner.