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Paper | Special issue | Vol 42, No. 1, 1996, pp.397-414
Published online, 1st January, 1970
DOI: 10.3987/COM-95-S55
Total Syntheses of BE-12406 A and Its C(8)-Vinyl Analog

Takamitsu Hosoya, Eiji Takashiro, Yasuko Yamamoto, Takashi Matsumoto, and Keisuke Suzuki

*Department of Chemistry, Keio University, 3-14-1, Hiyoshi, Kohoku, Yokohama 223-8522, Japan

Abstract

Total syntheses of BE-12406 A (3a) and its C(8)-vinyl analog (3c) are described. The key step is the selective O-glycosylation of naphthol (4)with L-rhamnopyranosyl fluoride (5) by employing Cp2HfCl2-AgClO4 in fluorobenzene at -20°C in the presence of a hindered base, 2,6-di-t-butyl-4-methylpyridine (12), affording O-glycoside (11) in good yield.