1338801-66-3Relevant articles and documents
Total synthesis of (+)-yohimbine via an enantioselective organocatalytic Pictet-Spengler reaction
Herle, Bart,Wanner, Martin J.,Van Maarseveen, Jan H.,Hiemstra, Henk
, p. 8907 - 8912 (2011)
The binolphosphoric acid-catalyzed Pictet-Spengler reaction of an N-(5-oxy-2,4-pentadienyl)tryptamine derivative with methyl 5-oxo-2- (phenylseleno)pentanoate leads to the tetrahydro-β-carboline in a 92:8 enantiomeric ratio. This product is easily converted into the substrate for a stereoselective intramolecular Diels-Alder reaction of the type earlier reported by Jacobsen. These two key steps constitute the basis for a nine-step total synthesis of (+)-yohimbine from tryptamine. A similar asymmetric Pictet-Spengler reaction was applied to the synthesis of an intermediate in the recent total synthesis of corynantheidine by Sato.
