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Pure Appl. Chem., 2000, Vol. 72, No. 9, pp. 1783-1786

Synthetic study of ravidomycin, a hybrid natural product

Keisuke Suzuki

Department of Chemistry, Tokyo Institute of Technology, and CREST, JST, 2-12-1, O-okayama, Meguro-ku, Tokyo 152-8551, Japan

Abstract: Strategies and tactics associated with the total synthesis of hybrid natural products are discussed. The target is ravidomycin (2), one of the gilvocarcin-class antitumor antibiotics with an aryl C-glycoside structure. The first total synthesis of 2, which was achieved along similar lines of that of gilvocarcin V (1), served for the determination of the relative as well as the absolute stereochemistry of 2. Also revealed was a limitation of the synthetic scheme so long as the amino sugar congener was concerned. A preliminary result is discussed on the [2+2+2] approach that relies on the ready availability of various benzocyclobutene derivatives via regioselective [2+2] cycloaddition of α-alkoxybenzynes and ketene silyl acetals.