Total synthesis of (+)-homopumiliotoxin 223G

Article abstract of DOI:10.1016/S0040-4039(98)00082-3

A new practical route for the first total synthesis of (+)- homopumiliotoxin 223G is described, in which the palladium-catalyzed carbonylation of the vinyl iodide, leading to efficient construction of the quinolizidine nucleus incorporating the (Z)-alkylidene side chain, is the key strategic clement. Another key feature of this synthesis involves the Lewis acid-induced chelation-controlled propargylation using the allenylsilane with complete diastereoselectivity.