1610617-17-8Relevant articles and documents
Synthesis of (S)- and (R)-harmicine from proline: An approach toward tetrahydro-β-carbolines
Lood, Christopher S.,Koskinen, Ari M. P.
, p. 2357 - 2364 (2014/04/17)
(S)- and (R)-Harmicine were synthesized from L- and D-proline, respectively. This chiral pool synthesis constitutes a new approach towards C1 substituted tetrahydro-β-carbolines. The developed route makes use of the 9-phenyl-9-fluorenyl protecting group strategy of amino acids to prevent racemization of the vulnerable α-amino carbonyl stereocenter. Enantiopure harmicine (> 99%ee) was obtained in nine steps from commercially available starting material. The synthesis was performed without the use of any silica gel flash chromatography.
