288159-10-4Relevant academic research and scientific papers
Asymmetric Synthesis of (R)-1-Alkyl-Substituted Tetrahydro-?-carbolines Catalyzed by Strictosidine Synthases
Pressnitz, Desiree,Fischereder, Eva-Maria,Pletz, Jakob,Kofler, Christina,Hammerer, Lucas,Hiebler, Katharina,Lechner, Horst,Richter, Nina,Eger, Elisabeth,Kroutil, Wolfgang
supporting information, p. 10683 - 10687 (2018/08/17)
Stereoselective methods for the synthesis of tetrahydro-?-carbolines are of significant interest due to the broad spectrum of biological activity of the target molecules. In the plant kingdom, strictosidine synthases catalyze the C?C coupling through a Pictet–Spengler reaction of tryptamine and secologanin to exclusively form the (S)-configured tetrahydro-?-carboline (S)-strictosidine. Investigating the biocatalytic Pictet–Spengler reaction of tryptamine with small-molecular-weight aliphatic aldehydes revealed that the strictosidine synthases give unexpectedly access to the (R)-configured product. Developing an efficient expression method for the enzyme allowed the preparative transformation of various aldehydes, giving the products with up to >98 % ee. With this tool in hand, a chemoenzymatic two-step synthesis of (R)-harmicine was achieved, giving (R)-harmicine in 67 % overall yield in optically pure form.
Enantiopure tetrahydro-β-carbolines via Pictet-Spengler reactions with N-sulfinyl tryptamines
Gremmen, Christiaan,Willemse, Bianca,Wanner, Martin J.,Koomen, Gerrit-Jan
, p. 1955 - 1958 (2007/10/03)
(Equation presented) The influence of N-sulfinyl chiral auxiliaries on the stereochemistry of the Pictet-Spengler reaction has been investigated. From enantiopure (R)-N-p-toluenesulfinyltryptamine a new and efficient route to enantiopure tetrahydro-β-carb
