A novel approach to the skeletons of the ergot alkaloids and secoergolines

Article abstract of DOI:10.1016/0040-4020(95)00830-2

An efficient eight-stage synthesis of N-benzenesulphonyl-3-(3'-methoxyprop-2'-en-1'-yl)-4-(1'-hydroxy-2'-tri methylsilylmethyl-prop-2'-en-1'-yl)-indoles from 4-carbomethoxyindole is described, together with the use of these benzylic alcohols for intramolecular cation-olefine cycloadditions that yield either a tetracyclic product (suitable for elaboration into ergot alkaloids) or a tricyclic product (suitable for elaboration into secoergolines) depending upon the reaction conditions.