Asymmetric synthesis of the spirocyclic core of the cylindricine-type alkaloids |
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| Affiliation: | 1. School of Natural Sciences-Chemistry, University of Tasmania, Hobart, Tasmania 7001, Australia;2. Australian Centre for Research on Separation Science (ACROSS), University of Tasmania, Hobart, Tasmania 7001, Australia;1. Laboratory of Natural Products Chemistry, Department of Chemistry, Faculty of Science, University of Dschang, P.O. Box 67, Dschang, Cameroon;2. Institute of Natural Medicine, University of Toyama, 2630-Sugitani, Toyama 930-0194, Japan;3. Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan;1. Division of Basic Neuroscience, Medicinal Chemistry Program, McLean Hospital, Belmont, MA 02478, United States;2. Department of Psychiatry, Harvard Medical School, Boston, MA 02115, United States |
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| Abstract: | Marine alkaloids from the cylindricine and lepadiformine families possess an interesting spirotricyclic skeleton. An intramolecular nitrone/olefin 1,3-dipolar cycloaddition has been used to form their spirocyclic 1-azaspiro[4.5]decane core in a regio- and stereoselective fashion. The cyclization precursor can be easily accessed using the asymmetric electrophilic hydroxyamination of enolate. |
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