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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 22, 1992 - Issue 19
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Original Articles

Synthesis of an Allylic Spiro-Lactone

Mauricio Gomes Constantino Departament de Química Faculdade de Filosofia Ciěncias e Lerras de Ribeir[acaron]o Preto, Universidade de São Paulo Av., Bandeirantes 3900, CEP 14049, Ribeirão Preto, SP, Brazil
,
Milton Beltrame Jr. Departament de Química Faculdade de Filosofia Ciěncias e Lerras de Ribeir[acaron]o Preto, Universidade de São Paulo Av., Bandeirantes 3900, CEP 14049, Ribeirão Preto, SP, Brazil
,
Edna Faria de Medeiros Departament de Química Faculdade de Filosofia Ciěncias e Lerras de Ribeir[acaron]o Preto, Universidade de São Paulo Av., Bandeirantes 3900, CEP 14049, Ribeirão Preto, SP, Brazil
&
Gil-Valdo Josè da Silva Departament de Química Faculdade de Filosofia Ciěncias e Lerras de Ribeir[acaron]o Preto, Universidade de São Paulo Av., Bandeirantes 3900, CEP 14049, Ribeirão Preto, SP, Brazil
Pages 2859-2864 | Received 29 May 1992, Published online: 23 Sep 2006
 
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Abstract

A synthesis of an allylic spiro-lactone (1) is described. Compound 1 is obtained in 5 steps from dimedone with an overall yield of 8.8%. The main feature of the synthesis is the transformation of compound 3 in 1, which involves an water elimination accompanied by allylic rearrangement and lactonization.

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