Synthesis of the diarylindolizidine alkaloid (+)-Fistulopsine B: Application of an organocatalytic Michael addition reaction. Issue 13 (29th March 2018)

• Record Type: Journal Article
• Authors: Moorthy, N.V.G.; Pansare, Sunil V.
• Is Part Of: Tetrahedron. Volume 74:Issue 13(2018)
• Page Start: 1422
• Page End: 1429
• Publication Date: 2018-03-29
• Subjects: Organocatalysis -- Arylindolizidine -- Michael addition -- Nitroketone -- Nitrone; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2018.01.032
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: The first synthesis of a recently isolated antiproliferative diarylindolizidine alkaloid, (+)-fistulopsine B, was achieved. The synthesis features the use of an organocatalytic ketone-nitrostyrene Michael addition as the key step. Graphical abstract: The first, enantioselective synthesis of the diaryl indolizidine alkaloid (+)-fistulopsine B was achieved from a key γ-nitroketone which is easily prepared by an organocatalytic Michael addition.