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Synthesis 2000; 2000(10): 1459-1463
DOI: 10.1055/s-2000-7112
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Synthesis of (1R,3R)-3-[2-(Aminoethyl)-2,2-dimethylcyclobutyl]methanol and (1S,3R)-(3-Amino-2,2-dimethylcyclobutyl)methanol from (+)-Nopinone

M. José Figueira* , J. Manuel Blanco, Olga Caamaño, Franco Fernández, Xerardo García-Mera, Carmen López
  • *Departamento de Química Orgánica, Facultad de Farmacia, Universidad de Santiago de Compostela, E-15706-Santiago de Compostela, Spain; Fax + 34(981)59 49 12; E-mail: qoolga@usc.es
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Publication Date:
31 December 2000 (online)

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The title amino alcohols 6 and 7, which are of interest as intermediates in the synthesis of carbocyclic analogs of nucleosides, were synthesized from (+)-nopinone (8). Ring opening of α-isonitrosonopinone leads to a cyanoester which can be directly reduced to 6. Alternatively, a longer route from the lactam 12, one of the Beckmann rearrangement products of 8, leads also to 6, in a higher overall yield. Besides this the isomeric lactam 13 was transformed, upon hydrolytic opening, oxidative degradation of the lateral chain and reduction, into 7.

lactams - amino acids - amino alcohols - carbocycles - nucleosides - terpenoids

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