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A New Method for the Synthesis of Stipitatic Acid Isomers: Photooxygenation of Ethyl 6 H ‐Cyclohepta[ d ][1,3]dioxole‐6‐carboxylate
Author(s) -
Dastan Arif,
Saracoglu Nurullah,
Balci Metin
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200109)2001:18<3519::aid-ejoc3519>3.0.co;2-2
Subject(s) - chemistry , photooxygenation , medicinal chemistry , triethylamine , bicyclic molecule , catalysis , thiourea , carboxylate , tetraphenylporphyrin , organic chemistry , photochemistry , porphyrin , singlet oxygen , oxygen
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 .