1,2,3,4-Tetrahydro-β-carbolines (THβCs) are a pharmacologically important group of compounds belonging to the indole alkaloids. C1-Substituted optically active THβCs have been the target of extensive synthetic efforts due to the presence of the scaffold in numerous natural products and synthetic targets. This review briefly summarizes the methods to obtain the C1 stereocenter and concentrates on evaluating the pharmacological importance of optically active C1-substituted THβCs, including their PDE5-inhibitory, antimalarial, antiviral and antitumor activities.

(2015). Synthesis of chiral 2-indolyl methanamines and insight into the stereochemistry protecting effects of the 9-phenyl-9-fluorenyl protecting group. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015(17) Keywords: Asymmetric synthesis / Amino acids / Chiral pool / Protecting groups Tetrahydro-β-carbolines, a privileged structural feature in natural products and pharmaceutically active compounds, has been the cause for considerable research interest, spanning many decades. Herein is reported the synthesis of the structurally closely related compounds denoted as (indol-2-yl)methanamines, in 99 % ee using amino acid starting materials, coupled with a 9-phenyl-9-fluorenyl (Pf) protect-

Synthesis of Chiral (Indol-2-yl)methanamines and Insight into the Stereochemistry ProtectingEffects of the 9-Phenyl-9-fluorenyl Protecting Group. -Whereas starting compound (III) is already known, an efficient approach to the analogous amino acid derivatives (I) and (V) is investigated to prepare them in a reasonable yield. All these 4 substrates, protected with the bulky Pfl group and available in an enantiomerically pure form, are transformed to the required title compounds (II), (IV), and (IX) as substructures of indole alkaloids. No racemization is observed in this ring-closing process and the following deprotection. Stereochemical effects in context with the Pfl protection are elaborated and discussed in detail. -(LOOD, C. S.; LAINE, A. E.; HOEGNAESBACKA, A.; NIEGER, M.; KOSKINEN*, A. M. P.; Eur. J. Org. Chem. 2015, 17, 3793-3805, http://dx.

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