Synthesis of the octahydroindole core of aeruginosins: a new bicyclic α-amino acid

The first synthesis of 6-hydroxyoctahydroindole-2-carboxylic acid derivatives with a cis fusion in the azabicyclic nucleus is described. The synthesis involves a Birch reduction of O-methyl-L-tyrosine followed by an aminocyclization in acid medium to give a mixture of 6-oxo-octahydroindole-2-carboxy...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 1996-07, Vol.7 (7), p.1899-1902
Main Authors: Bonjoch, Josep, Catena, Juanlo, Isábal, Esther, López-Canet, Meritxell, Valls, Nativitat
Format: Article
Language:English
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Summary:The first synthesis of 6-hydroxyoctahydroindole-2-carboxylic acid derivatives with a cis fusion in the azabicyclic nucleus is described. The synthesis involves a Birch reduction of O-methyl-L-tyrosine followed by an aminocyclization in acid medium to give a mixture of 6-oxo-octahydroindole-2-carboxylic acids 3 and 4, which could be separated after dibenzylation. Transesterification, hydrogenolysis in the presence of acetic anhydride and reduction of the amido ketones 9 and 10 provides the four stereoisomeric alcohols from which alcohol 14 showed nmr data very close to the aeruginosin 298-A core. (i) Li, NH 3, EtOH; (ii) HCl 3N; (iii) BrBn, NaHCO 3; (iv) MeOH, Dowex 1×8; (v) H 2/Pd(OH) 2, Ac 2O; (vi) LS-Selectride.
ISSN:0957-4166
1362-511X
DOI:10.1016/0957-4166(96)00225-X