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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 26, 1996 - Issue 1
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Original Articles

Improved Synthesis of Methyl 7,7-Ethylenedioxy-3-methyl-9-oxobicyclo[3.3.1]non-3-ene-1-carboxylate, Intermediate for the Synthesis of Huperzine A Analogues

Pelayo Camps Laboratori de Química Farmacèutica Facultat de Farmàcia, Universitat de Barcelona, Av. Diagonal, s/n. E-08028-, Barcelona, Spain
,
Joan Contreras Laboratori de Química Farmacèutica Facultat de Farmàcia, Universitat de Barcelona, Av. Diagonal, s/n. E-08028-, Barcelona, Spain
,
Mercè Font-Bardia Departament de Cristal.lografia, Mineralogia i Dipòsits Minerals, Facultat de Geologia, Universitat de Barcelona, Av. Martí Franqués, E-08028, Barcelona, Spain
&
Xavier Solans Departament de Cristal.lografia, Mineralogia i Dipòsits Minerals, Facultat de Geologia, Universitat de Barcelona, Av. Martí Franqués, E-08028, Barcelona, Spain
Pages 9-18 | Received 15 May 1995, Published online: 21 Aug 2006
 
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Abstract

The title compound 4 has been obtained in an improved yield, from 1 via alcohol 2a, which was dehydrated by pyrolytic syn-elimination of its derived thiocarbonate 2c. A trans-configuration of 2a and its stereoisomer 3a was established by X-ray diffraction analysis of their mesylates 2b and 3b.

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