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Paper | Special issue | Vol 42, No. 1, 1996, pp.219-228
Published online, 1st January, 1970
DOI: 10.3987/COM-94-S7-1
Syntheses of L-Phenylalanine Derivatives Containing a Sulfur Substituent at the 2-Position

Masashi Ohba, Masaaki Imasho, and Tozo Fujii

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


A full account is given of the chiral syntheses of sulfur-containing L-phenylalanine derivatives (8b,c), selected as key intermediates for the synthesis of models for the starfish alkaloid imbricatine (7), via a 5-step route starting from N,N-diethyl-3,5-dimethoxybenzamide (9). The key steps involve introduction of a sulfur substituent into 9 at the 2-position and construction of the chiral α-amino acid moiety in the chlorides (12b,c) by the “bis-lactim ether” method.