The stereochemistry of spiropiperidine cyclizations (histrionicotoxin,part I) |
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| Authors: | Micheal Glanzmann Chatchanok Karalai Bernd Ostersehlt Uwe Schön Christiane Frese Ekkehard Winterfeldt |
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| Institution: | Institut für Organische Chemie der Universität Hannover, Schneiderberg 1 B, D-3000 Hannover, West Germany |
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| Abstract: | The spirocyclization of straingt-chain triketo-intermediates, similar to possible biogenetic precursors of histrionicotoxin, is shown to be stereoselective, generating the non-natural configuration at C-2. Aiming at an sp2-center in this position, triketo-brassylic ester was treated with ammonia at room temperature and was shown to cleanly and efficiently yield a spiroketone. |
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