alpha,beta-Unsaturated Diazoketones as Platforms in the Asymmetric Synthesis of Hydroxylated Alkaloids. Total Synthesis of 1-Deoxy-8,8a-diepicastanospermine and 1,6-Dideoxyepicastanospermine and Formal Synthesis of Pumiliotoxin 251D
Contribuinte(s) |
UNIVERSIDADE DE SÃO PAULO |
---|---|
Data(s) |
05/11/2013
05/11/2013
2012
|
Resumo |
A versatile and concise approach for the stereoselective synthesis of mono-, di-, and trihydroxylated indolizidines is presented in four to six steps from Cbz-prolinal and a diazophosphonate. The key steps involved a Wolff rearrangement, followed by a stereoselective dihydroxylation/epoxidation reaction, from an alpha,beta-unsaturated diazoketone. The strategy also permits extension to the synthesis of many natural hydroxylated indolizidine alkaloids as demonstrated in the formal synthesis of pumiliotoxin 251D. FAPESP (Research Supporting Foundation of the State of Sao Paulo) FAPESP (Research Supporting Foundation of the State of Sao Paulo) [2012/04685-5, 2008/09653-9] CNPq [307905/2009-8, 160428/2011-4] CNPq |
Identificador |
JOURNAL OF ORGANIC CHEMISTRY, WASHINGTON, v. 77, n. 21, supl. 1, Part 6, pp. 9926-9931, 37561, 2012 0022-3263 http://www.producao.usp.br/handle/BDPI/40981 10.1021/jo301967w |
Idioma(s) |
eng |
Publicador |
AMER CHEMICAL SOC WASHINGTON |
Relação |
JOURNAL OF ORGANIC CHEMISTRY |
Direitos |
closedAccess Copyright AMER CHEMICAL SOC |
Palavras-Chave | #ENANTIOSELECTIVE SYNTHESES #WOLFF REARRANGEMENT #CASTANOSPERMINE #1-DEOXY-8,8A-DI-EPI-CASTANOSPERMINE #CHEMISTRY, ORGANIC |
Tipo |
article original article publishedVersion |