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Synthese der macrocyclischen Spermidin‐Alkaloide Oncinotin, Neooncinotin, Isooncinotin und Pseudooncinotin in racemischer Form. 159. Mitteilung über Alkaloide
Author(s) -
Guggisberg Armin,
Broek Peter Van Den,
Hesse Manfred,
Schmid Hans,
Schneider Fernand,
Bernauer Karl
Publication year - 1976
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.19760590839
Subject(s) - chemistry , piperidine , stereochemistry , bromide , derivative (finance) , spermidine , organic chemistry , financial economics , economics , enzyme
Synthesis of the Macrocyclic Spermidine Alkaloids Oncinotine, Neooncinotine, Isooncinotine and Pseudooncinotine in Racemic Forms . The four isomeric spermidine alkaloids ( Scheme 1 ) mentioned in the title were synthesized as follows: Reaction of the piperidine derivative 5 and the bromide 6 led to the intermediate 13 which was converted to (±)‐oncinotine (±‐ 1 ) and (±)‐pseudooncinotine (±‐ 4 ) ( Scheme 3 ). The analogous reaction of 5 and the isomeric bromid 7 gave the intermediate 22 from which (±)‐neooncinotine (±‐ 2 ) and (±)‐isooncinotine (±‐ 3 ) were synthesized ( Scheme 4 ). The overall yields were found to be between 22 (±‐ 1 ) and 54% (±‐ 3 ).