SYNTHESIS AND STEREOCHEMISTRY OF A-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-methylva lerolactim (3), O-methylcaprolactim (4) and O-methyl-4-t-butylcaprolac tim (5) with ethyl 6, -alpha-[1-(1,2,3,4-tetrahydro-isoquinolyl)]aceta te (1), 8, a-2,3-dimethoxygona-1,3,5(10),9(11)-tetraen-12-one (6) D-ho mo-derivatives (7-9), and medium-sized ring cyclic diamides (10,11) we re obtained The stereoselective reduction of compounds 6-9 by Adam's p latinum catalyst afforded 8, 13-diaza-2,3-dimethoxygona-1,3,5(10)-trie n-12-one (12) and its D-homo derivatives (13-15). The structures of th e compounds obtained were established by NMR and X-my crystallographic analyses. (C) 1998 by Elsevier Science Inc.