Premium
The Asymmetric Synthesis of the [D 8 ]‐Labeled (−)‐( S )‐Dihydroxyverbacine, the Terminal Precursor in the Biogenesis of the Macrobicyclic Spermine Alkaloids Aphelandrine and Orantine
Author(s) -
Nezbedová Lenka,
Drandarov Konstantin,
Werner Christa,
Hesse Manfred
Publication year - 2000
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(20001108)83:11<2953::aid-hlca2953>3.0.co;2-i
Subject(s) - chemistry , spermine , biogenesis , alkaloid , terminal (telecommunication) , stereochemistry , polyamine , biochemistry , enzyme , telecommunications , computer science , gene
The asymmetric synthesis of the unlabeled and [D 8 ]‐labeled terminal precursors, 4 ((−)‐( S )‐dihydroxyverbacine) and 19 , respectively, in the biogenesis of the spermine alkaloids aphelandrine ( 5 ) and orantine ( 6 ), respectively, is described. A partial synthesis of the alkaloid (−)‐( S )‐[( E )‐4‐methoxycinnamoyl]buchnerine ( 10 ) is also presented.