157397-50-7Relevant academic research and scientific papers
An efficient one-pot decarboxylative aromatization of tetrahydro-β-carbolines by using N-chlorosuccinimide: total synthesis of norharmane, harmane and eudistomins
Kamal, Ahmed,Sathish, Manda,Prasanthi,Chetna, Jadala,Tangella, Yellaiah,Srinivasulu, Vunnam,Shankaraiah, Nagula,Alarifi, Abdullah
, p. 90121 - 90126 (2015)
A facile method for the synthesis of a variety of β-carbolines and their natural products such as norharmane (2a), harmane (2b), eudistomins I, N, T, and U (6, 7, 9 and 10, respectively) has been successfully developed via a decorboxylative aromatization tool by employing N-chlorosuccinimide (NCS) as a mild and efficient reagent. Gratifyingly, this reagent system proceeds in a one-pot manner and converted all the tetrahydro-β-carboline acids into their corresponding decorboxylative aromatic products with good to excellent yields. Additionally, this system works well in the case of tetrahydro-β-carboline esters to produce their aromatic partners in high yields.
Diastereoselective Pictet-Spengler Reactions of L-(Boc)Phenylalaninal and L-(Boc)Prolinal: Biomimetic Syntheses of Eudistomin T and (-)-Woodinine
McNulty, James,Still, Ian W. J.
, p. 1329 - 1338 (2007/10/02)
The diastereoselective Pictet-Spengler reaction of L-(Boc)phenylalaninal with tryptamine and the elaboration of this intermediate to the antibacterial compound eudistomin T and analogues of the antileukaemic compound eudistomidin B are described.We also report an efficient synthesis of the naturally occuring alkaloid (-)-woodinine from L-(Boc)prolinal and 5-bromotryptamine in three steps, using a diastereoselective Pictet-Spengler reaction.This approach affords, in addition, formal synthesis of the marine alkaloids eudistomins H and I.
