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

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

Tetrahedron, cilt.64, sa.30-31, ss.7289-7294, 2008 (SCI-Expanded, Scopus)

Yayın Türü: Makale / Tam Makale
Cilt numarası: 64 Sayı: 30-31
Basım Tarihi: 2008
Doi Numarası: 10.1016/j.tet.2008.05.066
Dergi Adı: Tetrahedron
Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
Sayfa Sayıları: ss.7289-7294
Bilecik Şeyh Edebali Üniversitesi Adresli: Hayır

Özet

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.