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Biomimetic Formation of Macrocyclic Spermine Alkaloids
Author(s) -
Dimitrov Vladimir,
Geneste Hervé,
Guggisberg Armin,
Hesse Manfred
Publication year - 2001
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 - 10.1002/1522-2675(20010711)84:7<2108::aid-hlca2108>3.0.co;2-g
Subject(s) - chemistry , atmospheric pressure chemical ionization , oxidizing agent , mass spectrometry , oxidative coupling of methane , phenol , chloride , intramolecular force , hemin , spermine , chromatography , high performance liquid chromatography , ionization , chemical ionization , organic chemistry , combinatorial chemistry , heme , ion , enzyme , methane
Dihydroxyverbacine ( 10 ), a precursor for oxidative phenol coupling, was obtained via (±)‐buchnerine ( 14 ), whose synthesis is described. The oxidizing system hemin (ferriprotoporphyrin IX chloride)/H 2 O 2 promoted intramolecular coupling of 10 to give the alkaloids aphelandrine ( 1 ), orantine ( 2 ), and chaenorpine ( 7 ). The alkaloids were identified by on‐line coupled HPLC and atmospheric‐pressure chemical‐ionization (APCI) mass spectrometry.