Synthesis of cyclopropane-annulated conduritol derivatives: norcaran-2,3,4,5-tetraoles

ŞENGÜL, Mustafa; Menzek, Abdullah; ŞAHİN, Ertan; ARK, MUSTAFA; SARAÇOĞLU, Nurullah

doi:10.1016/j.tet.2008.05.066

Synthesis of cyclopropane-annulated conduritol derivatives: norcaran-2,3,4,5-tetraoles

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ŞENGÜL M., Menzek A., ŞAHİN E., ARK M., SARAÇOĞLU N.

Tetrahedron, vol.64, no.30-31, pp.7289-7294, 2008 (SCI-Expanded)

Publication Type: Article / Article
Volume: 64 Issue: 30-31
Publication Date: 2008
Doi Number: 10.1016/j.tet.2008.05.066
Journal Name: Tetrahedron
Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
Page Numbers: pp.7289-7294
Bilecik Şeyh Edebali University Affiliated: No

Abstract

Norcaran-2,3,4,5-tetraoles were synthesized starting from methyl 1,3,5-cycloheptatriene-7-carboxylate in several steps. Norcaradiene endoperoxide is the key component; it was obtained by photooxygenation of methyl 1,3,5-cycloheptatriene-7-carboxylate. The other oxygen functionalities are introduced through epoxide ring opening and OsO4-hydroxylation reactions. © 2008 Elsevier Ltd. All rights reserved.