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Formation of the First Trimeric Monoterpenoid Indole Alkaloids
Author(s) -
Schübel Helmut,
Fahn Walter,
Stöckigt Joachim
Publication year - 1989
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19890720119
Subject(s) - chemistry , indole alkaloid , alkaloid , indole test , stereochemistry , catharanthus roseus , organic chemistry , biochemistry
Under O 2 , the Aspidosperma alkaloid tabersonine ( 1 ) was converted by a crude enzyme preparation from leaves of mature plants of Catharanthus roseus G D ON into the trimeric 3‐hydroxy‐14′‐(3α″‐tabersonyl)voafrine B ( 4 ) which was easily reduced by NaBH 4 to 14′‐(3α″‐tabersonyl)voafrine B ( = tertabersonine; 5 ). Compounds such as 4 and 5 are the first trimeric alkaloids in the series of monoterpenoid indole alkaloids.