Synthesis and stereochemistry of 8,13-diaza-2,3-dimethoxygona-1,3,5(10),9(11)-tetraen-12-one and D-homo derivatives.

From the condensation reaction of O-methylbutyrolactim (2), O-methylvalerolactim (3), O-methylcaprolactim (4) and O-methyl-4-t-butylcaprolactim (5) with ethyl 6, 7-dimethoxy-alpha-[1-(1,2,3,4-tetrahydro-isoquinolyl)]acetate (1), 8, 13-diaza-2,3-dimethoxygona-1,3,5(10),9(11)-tetraen-12-one (6) D-homo-derivatives (7-9), and medium-sized ring cyclic diamides (10,11) were obtained The stereoselective reduction of compounds 6-9 by Adam's platinum catalyst afforded 8, 13-diaza-2,3-dimethoxygona-1,3,5(10)-trien-12-one (12) and its D-homo derivatives (13-15). The structures of the compounds obtained were established by NMR and X-my crystallographic analyses. (C) 1998 by Elsevier Science Inc.