146681-76-7Relevant articles and documents
Synthesis of Vinca Alkaloids and Related Compounds. 63. A New Synthetic Pathway for Preparing Alkaloids and Related Compounds with the Aspidosperma Skeleton. Total Syntheses of (+/-)-Vincadifformine, (+/-)-Tabersonine, and (+/-)-3-Oxotabersonine
Kalaus, Gyoergy,Greiner, Istvan,Kajtar-Peredy, Maria,Brlik, Janos,Szabo, Lajos,Szantay, Csaba
, p. 1434 - 1442 (2007/10/02)
Compound 3, which has an indole skeleton containing a masked acryl ester function, was synthesized from the hydrochloride of (2-ethoxycarbonyl)tryptamine (2).The cycloaddition of 3 with methyl 4-formylhexanoate (21) or with 5-(benzoyloxy)-2-ethylpentanal (33) yielded the starting materials for target compounds (+/-)-vincadifformine (4), (+/-)-3-oxotabersonine (42), and (+/-)-tabersonine (43).The synthesis of vincadifformine (4) was achieved in two different ways: via 3-oxovincadifformine (7) and via tricyclic benzoate esters 37 and 38.The double bond required in tabersonine (43) and 3-oxotabersonine (42) was introduced by treatment of 3-thioxovincadifformine (39) with p-toluenesulfinyl chloride.