Radical induced fragmentation in a benzoxocane ring system: application to the synthesis of elvirol and a formal synthesis of 7,8-dihydroxycalamenene |
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Authors: | Amalesh Roy Kazi Tuhina Bidyut Biswas Ramanathapuram V Venkateswaran |
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Institution: | 1. Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Kollkata 700 032, India;2. Department of Chemistry, B.S. College, S-24 P.G.S., Canning 743329, WB, India |
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Abstract: | A novel radical induced fragmentation in a benzoxocane ring system has been employed for a synthesis of elvirol 8 and an advanced intermediate in the synthesis of 7,8-dihydroxycalamenene 20. The coumarins 9, 22 were taken through a sequence of reactions to the benzoxocanols 16, 30, which when subjected to Barton’s deoxygenation conditions involving conversion to the corresponding thionocarbonates 17, 31 followed by exposure to tri-n-butyltin hydride, underwent a radical induced fragmentation to furnish elvirol 8 and the curcuphenol derivative 32, which was converted to the dimethoxy compound 33. This had served as an advanced intermediate in a previous synthesis of dihydroxycalamenene. |
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