Utilization of a Michael addition: dipolar cycloaddition cascade for the synthesis of (+/-)-cylindricine C |
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Authors: | Flick Andrew C Caballero Maria José Arevalo Padwa Albert |
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Affiliation: | Department of Chemistry, Emory University, Atlanta, GA 30322, USA. |
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Abstract: | A new approach to the marine alkaloid (+/-)-cylindricine C has been devised. The key element of the synthesis consists of a Michael addition/dipolar cycloaddition cascade between 2,3-bis(phenylsulfonyl)-1,3-butadiene and 9-triisopropylsilanyloxy-non-1-en-5-one oxime. The resulting cycloadduct was converted into (+/-)-cylindricine C by a sequence of reactions including a reductive cyclization, intramolecular enolate alkylation, and conjugate addition to introduce the n-hexyl side chain. |
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