Total synthesis of (+/-)-dihydroactinidiolide using selenium-stabilized carbenium ion
| Contribuinte(s) |
UNIVERSIDADE DE SÃO PAULO |
|---|---|
| Data(s) |
19/10/2012
19/10/2012
2009
|
| Resumo |
A new, short total synthesis of dihydroactinidiolide 1 is described using selenium carbenium ion-promoted carbon-carbon bond formation as the key step. Our synthetic strategy starts with a lactonization reaction between 1,3,3-trimethylcyclohexene 13 and alpha-chloro-alpha-phenylseleno ethyl acetate 14, affording the key intermediate, alpha-phenylseleno-gamma-butyro lactone 15, which reacted via a selenoxide elimination to the target compound 1. (C) 2009 Elsevier Ltd. All rights reserved. FAPESP CAPES FAPERGS FUNDECT-MS CNPq |
| Identificador |
TETRAHEDRON LETTERS, v.50, n.40, p.5569-5571, 2009 0040-4039 http://producao.usp.br/handle/BDPI/20858 10.1016/j.tetlet.2009.07.067 |
| Idioma(s) |
eng |
| Publicador |
PERGAMON-ELSEVIER SCIENCE LTD |
| Relação |
Tetrahedron Letters |
| Direitos |
closedAccess Copyright PERGAMON-ELSEVIER SCIENCE LTD |
| Palavras-Chave | #Dihydroactinidiolide #Selenium carbenium ions #Organoselenium compounds #GAMMA-BUTYROLACTONES #DIHYDROACTINIDIOLIDE #CHEMISTRY #(-)-ACTINIDIOLIDE #CAROTENOIDS #ENANTIOMERS #PHEROMONE #LACTONE #ALKENES #TOBACCO #Chemistry, Organic |
| Tipo |
article original article publishedVersion |
