Total synthesis of (-)-indolizidine 167B via an unusual Wolff rearrangement from an alpha,beta-unsaturated diazoketone
| Contribuinte(s) |
UNIVERSIDADE DE SÃO PAULO |
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| Data(s) |
01/11/2013
01/11/2013
2012
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| Resumo |
A concise synthesis of the (-)-indolizidine alkaloid 167B and two formal syntheses of (-)-indolizidine 209D and (-)-coniceine are described in just three steps from an alpha,beta-unsaturated diazoketone, via an unusual photochemical Wolff rearrangement. Preparation of the unsaturated diazoketone is straightforward from N-Cbz-prolinal and a 3-diazo-2-oxopropylphosphonate, employing a Horner-Wadsworth-Emmons reaction. The strategy should be feasible and easily adaptable to the synthesis of other indolizidine alkaloids and analogues. (C) 2011 Elsevier Ltd. All rights reserved. FAPESP (Research Supporting Foundation of the State of Sao Paulo) FAPESP (Research Supporting Foundation of the State of Sao Paulo) CNPq CNPq |
| Identificador |
TETRAHEDRON LETTERS, OXFORD, v. 53, n. 7, supl. 1, Part 1, pp. 876-878, FEB 15, 2012 0040-4039 http://www.producao.usp.br/handle/BDPI/37276 10.1016/j.tetlet.2011.12.029 |
| Idioma(s) |
eng |
| Publicador |
PERGAMON-ELSEVIER SCIENCE LTD OXFORD |
| Relação |
TETRAHEDRON LETTERS |
| Direitos |
closedAccess Copyright PERGAMON-ELSEVIER SCIENCE LTD |
| Palavras-Chave | #INDOLIZIDINE ALKALOIDS #UNSATURATED DIAZOKETONES #WOLFF REARRANGEMENT #ARNDT-EISTERT HOMOLOGATION #PHOTOCHEMICAL #QUINOLIZIDINE ALKALOIDS #ENANTIOSELECTIVE SYNTHESES #INDOLIZIDINE ALKALOIDS #ANALOGS #ACIDS #CHEMISTRY, ORGANIC |
| Tipo |
article original article publishedVersion |
