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First Practical and Efficient Synthesis of 3‐Phosphorylated β‐Carboline Derivatives Using the Pictet–Spengler Reaction
Author(s) -
ViverosCeballos José Luis,
Sayago Francisco J.,
Cativiela Carlos,
Ordóñez Mario
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403418
Subject(s) - pictet–spengler reaction , chemistry , reaction conditions , organic chemistry , combinatorial chemistry , catalysis
We report here the first practical and efficient synthesis of the diethyl 1,2,3,4‐tetrahydro‐β‐carboline‐3‐phosphonates 3 and 4 as well as diethyl 9 H ‐β‐carboline‐3‐phosphonates 5 and 6 . The target compounds were prepared in good yields by application of the Pictet–Spengler reaction of easily obtainable phosphotryptophan diethyl ester 7 . The procedure is based on simple preparation of racemic 7 followed by a Pictet–Spengler reaction with several aldehydes and subsequent oxidation chemistry.