A practical synthesis of (+/-)-alpha-isosparteine from a tetraoxobispidine core |
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Authors: | Blakemore Paul R Kilner Colin Norcross Neil R Astles Peter C |
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Affiliation: | Department of Chemistry, Oregon State University, Corvallis, Oregon 97331-4003, USA. paul.blakemore@science.oregonstate.edu |
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Abstract: | [reaction: see text] The title alkaloid was synthesized in racemic form from 3,7-diallyl-2,4,6,8-tetraoxo-3,7-diazabicyclo[3.3.1]nonane (7) by a regioselective diallylation reaction followed by double ring-closing olefin metathesis and exhaustive reduction. Tetraoxobispidine 7 was itself prepared in three simple operations from dimethyl malonate. The entire sequence to alpha-isosparteine was conducted on a multigram scale and proceeded without recourse to chromatography. |
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