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 a-alkoxybenzynes and
ketene silyl acetals.
*Lecture presented at the 13th International
Conference on Organic Synthesis (ICOS-13), Warsaw, Poland, 1-5 July
2000.
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