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Investigations on the Chemistry of Berbanes, XII. Synthesis of Pseudo‐Depyrroloyohimbine Analogues
Author(s) -
Tóth István,
Bozsár Gabriella,
Szabó Lajos,
BaitzGács Eszter,
Tamás József,
Szántay Csaba
Publication year - 1987
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198719870315
Subject(s) - chemistry , nitrile , phosphonate , hydrolysis , condensation , catalytic hydrogenation , catalysis , organic chemistry , combinatorial chemistry , stereochemistry , physics , thermodynamics
The known keto nitrile 1 reacts with the phosphonate 2 to give the three isomers 3, 4 , and 5 . Catalytic reduction of 4 affords 6 and 7a . By hydrolysis and subsequent esterification of 7a the corresponding methyl ester 7b is obtained. Dieckmann condensation of 7b leads to the pseudoberbanes 9a, 9b . The stereochemistry of the compounds was proved by physical (NMR, IR, MS) and chemical methods.