Département de chimie moléculaire

Friedel-Crafts acetylation of the (R)-hexahydropyrroloindolizine I with AcCl in CH2Cl2 contg. AlCl3 gave only the diacetylated product II, whereas Vilsmeier-Haack acylation of I with RCONMe2/POCl3 (R = H, Me) in ethylene dichloride was regioselective and gave mainly the C-4 substituted monoacylhexahydropyrroloindolizines III. III (R = H) underwent consecutive MeLi methylation/LiAlH4 redn., C-3 formylation, and Wittig ethylidenation to give a mixt. of the Myrmicaria alkaloids M215A/M215B (IV). [on SciFinder(R)]