PDF herunterladen
Synthesis 2000; 2000(7): 949-952
DOI: 10.1055/s-2000-6289
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 Substituted 1,6-Dioxaspiro[3.4]octanes from 3-Chloro-2-(chloromethyl)prop-1-ene

Francisco Alonso* , Larry R. Falvello, Phillip E. Fanwick, Emilio Lorenzo, Miguel Yus
  • *Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain; Fax +34(96)5903549; E-mail: yus@ua.es; URL: http://www.ua.es/dept.quimorg/
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
31. Dezember 2000 (online)

  als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

The naphthalene-catalysed lithiation of 3-chloro-2-(chloromethyl)prop-1-ene, in the presence of symmetrically substituted ketones, led to the corresponding methylenic homoallylic diols, which upon treatment with iodine and silver(I) oxide in dioxane/water furnished a series of 1,6-dioxaspiro[3.4]octanes. These compounds are structural units present in some natural compounds such as clementeins and subexpinnatins.

3-chloro-2-(chloromethyl)prop-1-ene - naphthalene-catalysed lithiation - iodine/silver oxide induced cyclisation - 1,6-dioxaspiro[3.4]octanes