Enantioselective total synthesis of tricyclic myrmicarin alkaloids.

ABSTRACT: [reaction: see text] An enantioselective gram-scale synthesis of a key dihydroindolizine intermediate for the preparation of myrmicarin alkaloids is described. Key transformations in this convergent approach include a stereospecific palladium-catalyzed N-vinylation of a pyrrole with a vinyl triflate, a copper-catalyzed enantioselective conjugate reduction of a beta-pyrrolyl enoate, and a regioselective Friedel-Crafts reaction. The synthesis of optically active and isomerically pure samples of (4aR)-myrmicarins 215A, 215B, and 217 in addition to their respective C4a-epimers is presented.

SUBMITTER: Movassaghi M 

PROVIDER: S-EPMC2992882 | biostudies-literature | 2005 Sep

REPOSITORIES: biostudies-literature