Intramolecular Heck reaction strategy for the synthesis of functionalised tetrahydroanthracenes: a facile formal total synthesis of the linear abietane diterpene, umbrosone |
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Authors: | Sujaya Sengupta |
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Institution: | Division of Medicinal Chemistry, Indian Institute of Chemical Biology, 4 Raja S. C. Mullick Road, Kolkata 700 032, India |
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Abstract: | Rapid annulation employing an intramolecular Heck reaction yielded the functionalised 1,1,10-trimethyl-6-methoxy-1,2,3,4-tetrahydroanthracene 4a, a key intermediate for the linear diterpenoid quinone umbrosone (1), and the related compounds 4b-d. A similar strategy was also successfully adopted for the synthesis of the 9-methyl tetrahydroanthracene ester 5 and the tetrahydrodibenzoa,d]cycloheptene ester 6. |
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Keywords: | Heck reaction Tetrahydroanthracene Umbrosone Suzuki coupling 7-endo Heck cyclisation Benzocycloheptadiene |
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