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

Date

2001-09-01

Author

Dastan, A
Saracoglu, N
Balcı, Metin

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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,

Subject Keywords

Peroxides, Fused-ring systems, Natural products, Singlet oxygen, Photochemistry

URI

https://hdl.handle.net/11511/53263

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Collections

Graduate School of Natural and Applied Sciences, Article

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Citation Formats

A. Dastan, N. Saracoglu, and M. Balcı, “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, pp. 3519–3522, 2001, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/53263.