Enantioselective total synthesis of vicenistatin, a novel 20-membered macrocyclic lactam antitumor antibiotic

…, H Itoh, T Nakayama, S Horiuchi, T Eguchi…

Index: Matsushima, Yoshitaka; Itoh, Hiroaki; Nakayama, Takuya; Horiuchi, Sayo; Eguchi, Tadashi; Kakinuma, Katsumi Journal of the Chemical Society. Perkin Transactions 1, 2002 ,  # 7  p. 949 - 958

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Abstract

Enantioselective total synthesis of an antitumor antibiotic, vicenistatin, featuring a 20- membered macrocyclic lactam glycoside with the amino sugar vicenisamine, has been achieved. Key reactions in the synthesis of macrolactam aglycone involved Suzuki cross- coupling and Evans asymmetric aldol reaction. Penultimate glycosidation of the O-TMS- aglycone with appropriately protected 1-O-acetyl amino sugar and final deprotection ...