Syntheses of 1-phenylalanine derivatives containing a sulfur substituent at the 2-position

Article abstract of DOI:10.3987/com-94-s7-1

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.