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Synthesis of Tenuilobine, a Bis‐polyamine Alkaloid from Oncinotis tenuiloba , and Its Transamidation to Isotenuilobine
Author(s) -
Doll Martin K.H.,
Guggisberg Armin,
Hesse Manfred
Publication year - 1996
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.19960790221
Subject(s) - chemistry , polyamine , alkaloid , high performance liquid chromatography , base (topology) , two dimensional nuclear magnetic resonance spectroscopy , stereochemistry , combinatorial chemistry , organic chemistry , biochemistry , mathematical analysis , mathematics
From the leaves of Oncinotis tenuiloba S TAPF , a novel polyamine alkaloid, tenuilobine ( 9 ), was isolated. This paper presents the synthesis of 9 , as well as the base‐catalyzed Zip reaction of 9 , leading to the transamidation product isotenuilobine ( 10 ). The structure of 10 was further confirmed by 2D‐NMR correlation spectroscopy. For analytical purposes, the bis‐polyamines 9 and 10 were converted into their pentaacetyl derivatives 12 and 11 , respectively, which were readily separable by reverse‐phase HPLC.