Highly regioselective Vilsmeier-Haack acylation of hexahydropyrroloindolizine.

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)]

Références

Titre
Highly regioselective Vilsmeier-Haack acylation of hexahydropyrroloindolizine.
Type de publication
Article de revue
Année de publication
2001
Revue
J. Org. Chem.
Volume
66
Pagination
2522–2525
ISSN
0022-3263
Soumis le 12 avril 2018