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Towards a New Synthetic Entry into the Iboga ‐Alkaloid Family
Author(s) -
Frauenfelder Christine,
Borschberg HansJürg
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(20000809)83:8<1753::aid-hlca1753>3.0.co;2-g
Subject(s) - chemistry , cycloaddition , intramolecular force , olefin fiber , nitrone , derivative (finance) , retrosynthetic analysis , yield (engineering) , indole alkaloid , stereochemistry , substitution (logic) , flexibility (engineering) , alkaloid , combinatorial chemistry , indole test , total synthesis , organic chemistry , programming language , materials science , statistics , mathematics , computer science , financial economics , economics , catalysis , metallurgy , polymer
A novel retrosynthetic concept is presented that, in principle, allows access to many hitherto not accessible representatives of the Iboga ‐alkaloid family. The flexibility required by this approach is provided through a highly convergent assembly of the target, which allows for a control over the substitution pattern of the indole sub‐system, as well as over the relative configuration of the aliphatic core of these alkaloids. The key step for the construction of the latter consists in an intramolecular nitrone‐olefin 1,3‐dipolar cycloaddition reaction of 26 to yield the crucial tricyclic isoxazolidine derivative 28 .