Synthesis of Homoerythrinan Alkaloids of 1(2)-Alkene and 1, 6-Diene Types : Total Synthesis of Comosine, Dihydroschelhammeridine, Schelhammeridine, and 3-Epischelhammeridine

Abstract

Total syntheses of homoerythrinan alkaloids of 1(2)-alkene type, dihydroschelhammeridine and comosine, and those of 1, 6-dienoid type, schelhammeridine and 3-epischelhammeridine, were achieved. Total synthesis of the former alkaloids provided definite proof of their A/B-cis stereochemistry. In relatin to the stereochemistry, the conformations of erythrinan and homoerythrinan alkaloids are discussed.