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

Article abstract of DOI:10.1080/00397919608003857

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.

Full text of DOI:10.1080/00397919608003857

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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 a , Joan Contreras a , Mercè Font-
Bardia b & Xavier Solans b
a Laboratori de Química Farmacèutica Facultat
de Farmàcia , Universitat de Barcelona , Av.
Diagonal, s/n. E-08028-, Barcelona, Spain
b Departament de Cristal.lografia, Mineralogia
i Dipòsits Minerals, Facultat de Geologia ,
Universitat de Barcelona , Av. Martí Franqués,
E-08028, Barcelona, Spain
Published online: 21 Aug 2006.
To cite this article: Pelayo Camps , Joan Contreras , Mercè Font-Bardia & Xavier
Solans (1996) 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, Synthetic Communications: An International Journal
for Rapid Communication of Synthetic Organic Chemistry, 26:1, 9-18, DOI:
10.1080/00397919608003857

To link to this article: http://dx.doi.org/10.1080/00397919608003857
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