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
- Auteurs
- Sayah, Babak, Pelloux-Leon Nadia, Milet Anne, Pardillos-Guindet Josephine, and Vallee Yannick.
- Revue
- J. Org. Chem.
- Volume
- 66
- Pagination
- 2522–2525
- ISSN
- 0022-3263
Soumis le 12 avril 2018