Synthesis of natural (−)-hamigeran B |
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Authors: | Derrick LJ Clive Jian Wang |
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Institution: | Chemistry Department, University of Alberta, Edmonton, Alberta T6G 2G2, Canada |
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Abstract: | Alkylation of lactam 10, first with iodide 15 and then with MeI, gave mainly (18:1) lactam 18. This was converted by treatment with t-BuLi and then with aqueous base into enone 4, which was elaborated into (−)-hamigeran B. A key feature of the last part of the synthesis is the use of t-BuMe2Si-groups (as in intermediate 24) both to direct hydrogenation from the appropriate face and to protect the benzylic CO bond from hydrogenolysis. |
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Keywords: | hamigeran B Meyers&rsquo lactam hydrogenolysis silyl groups |
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