A new method for the synthesis of stipitatic acid isomers: Photooxygenation of ethyl 6H-cyclohepta[d][1,3]dioxole-6-carboxylate

Authors
Dastan, A Saracoglu, N Balci, M
Citation
A. Dastan et al., A new method for the synthesis of stipitatic acid isomers: Photooxygenation of ethyl 6H-cyclohepta[d][1,3]dioxole-6-carboxylate, EUR J ORG C, (18), 2001, pp. 3519-3522
Citations number
31
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
18
Year of publication
2001
Pages
3519 - 3522
Database
ISI
SICI code
1434-193X(200109):18<3519:ANMFTS>2.0.ZU;2-9
Abstract
Photooxygenation of the cycloheptatriene derivative 9 gave the bicyclic end operoxide 14. Cleavage of the peroxide linkage in 14 with thiourea resulted in the formation of 16. Treatment of the endoperoxide 14 with a catalytic amount of triethylamine provided a new isomer of stipitatic acid 11, and 16 . Pyrolysis or the CoTPP (TPP = tetraphenylporphyrin) catalyzed reaction of 14 resulted in the formation of iso-stipitatic acid 10, and 18,