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Communication | Special issue | Vol 33, No. 1, 1992, pp.21-26
Published online, 1st January, 1970
DOI: 10.3987/COM-91-S2
Synthesis of 5-Arylthio-3-Methyl-L-histidine, a Model for the Starfish Alkaloid Imbricante

Massashi Ohba, Takafumi Mukaihara, and Tozo Fujii*

*Faculty of Pharmaceutical Scicences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan

Abstract

Syntheses of 3-methyl-5-phenylthio-L-histidine (8a) and 3-methyl-5-(1-naphthy1)thio-L-histidine (8b), selected as models for the asteroid alkaloid imbricatine (7), have now become feasible through a 10-step route starting from 4(5)-bromoimidazole (9). The key steps involve replacement of the 4-bromo group by an arylthio group in the aldehyde (14) and construction of the L-alanine moiety in the chlorides (17a,b) by the “bis-lactim ether” method.