A new method for the synthesis of stipitatic acid isomers: Photooxygenation of ethyl 6H-cyclohepta[d][1,3]dioxole-6-carboxylate
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, no.18, pp.3519-3522, 2001 (SCI-Expanded, Scopus)
- Publication Type: Article / Article
- Publication Date: 2001
- Journal Name: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
- Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
- Page Numbers: pp.3519-3522
- Keywords: peroxides, fused-ring systems, natural products, singlet oxygen, photochemistry, BICYCLIC ENDOPEROXIDES
- Middle East Technical University Affiliated: No
Abstract
Photooxygenation of the cycloheptatriene derivative 9 gave the bicyclic endoperoxide 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,