Download PDF
Synthesis 1996; 1996(2): 281-284
DOI: 10.1055/s-1996-4191
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Synthesis of (1’S,3’R)-3-(3’-Amino-2’,2’-dimethylcyclobutyl)propan-1-ol from (-)-β-Pinene

José M. Blanco, Olga Caamaño, Franco Fernández* , Generosa Gómez, Isabel Nieto
  • *Departamento de Química Orgánica, Facultad de Farmacia, Universidad de Santiago, E-15706 Santiago de Compostela, Spain, Fax 34(9)81594912, E-mail qofranco@uscmail.usc.es
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

The title compound 3, a useful intermediate in the synthesis of carbocyclic analogs of nucleosides was synthesized from (-)-β-pinene (4) in seven steps: oxidation of 4 to (+)-nopinone (5); Beckmann rearrangement of the oxime-O-sulfonic acid of 5 to the bicyclic lactam 7 (a two-step procedure via oxime 6 is also described); hydrolytic ring opening of 7 to form amino acid • HCl 8; and reduction of the corresponding protected methyl ester 10 followed by deprotection. Overall yield, 67% from lactam 7.

(-)-β-pinene - (+)-nopinone - Beckmann rearrangement - hydroxylamine-O-sulfonic acid - carbocyclic nucleosides

      >