155106-26-6Relevant articles and documents
Formal synthesis of two Elaeocarpus alkaloids: elaeocarpine and isoelaeocarpine
Michael, Joseph P.,Parsons, Andrew S.
, p. 65 - 69 (2007/10/02)
1-(3-Acetoxypropyl)pyrrolidine-2-thione 7, prepared by acetylation and thionation of the readily accessible 1-(3-hydroxypropyl)pyrrolidin-2-one 5, undergoes Eschenmoser alkylidenation (sulfide contraction) with two phenacyl bromides to give the vinylogous amides (E)-1-(3-acetoxypropyl)-2-benzoylmethylenepyrrolidine 8 and the corresponding 2-methoxy-6-methylbenzoyl analogue 14.Reduction of the latter with lithium aluminium hydride yields 1-(3-hydroxypropyl)-2-(2-methoxy-6-methylbenzoyl)methylpyrrolidine 12, thereby completing a formal synthesis of the Elaeocarpus alkaloids elaeocarpine 10 and isoelaeocarpine 11.