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Investigations on the Chemistry of Berbanes, XII. Synthesis of Pseudo-Depyrroloyohimbine Analogues

✍ Scribed by Tóth, István ;Bozsár, Gabriella ;Szabó, Lajos ;Baitz-Gács, Eszter ;Tamás, József ;Szántay, Csaba

Publisher
John Wiley and Sons
Year
1987
Tongue
English
Weight
500 KB
Volume
1987
Category
Article
ISSN
0947-3440

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✦ Synopsis

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 estetificarion of 7r the corresponding methyl ester 7b is obtained. Dieckmaun condensation of 7b leads to the pseudoberbanes 9% 9b. The stereochemistry of the compounds was proved by physical (NMR IR, MS) and chemical methods.

Many normal2), all^-^), and epiallo-berbane4' stereoisomers with interesting pharmacological activity have been synthesized. However, the synthesis of the pseudoberbane skeleton has not yet been reported.

The normal, allo-, and epiallo-berbane skeletons have been prepared from the readily available racemic keto nitrile 1 ' I. This paper reports the synthesis of the pseudoberbane skeleton from the same keto nitrile.

To build up the fourth ring, the keto nitrile 1 was treated with the phosphonate 2 in the presence of KOtBu in DMF

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