A Novel Approach to Bicyclic Alkaloids Using a Tandem Diastereoselective Acyliminocyclization and Retro Diels-Alder Reaction Sequence. Synthesis of (+)-Indolizidine and (+)-Laburnine

Article abstract of DOI:10.1246/cl.1991.2135

A new aproach to diastereoselective cationic cyclization by stereocontrol due to the bicyclo<2.2.1>heptene moiety in a chiral γ-hydroxy lactam is described.The diastereoselective reaction followed by Diels-Alder cycloreversion has ben succesfully applied to a chiral synthesis of (+)-indolizidine and (+)-laburnine (=trachelanthamidine).