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

doi:10.1055/s-2000-6289

Synthesis 2000; 2000(7): 949-952
DOI: 10.1055/s-2000-6289

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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/

Abstract

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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

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