An unusual Michael-induced skeletal rearrangement of a bicyclo[3.3.1]nonane framework of phloroglucinols to a novel bioactive bicyclo[3.3.0]octane.
Org Lett
; 15(21): 5404-7, 2013 Nov 01.
Article
em En
| MEDLINE
| ID: mdl-24117171
ABSTRACT
A novel skeletal rearrangement of bicyclo[3.3.1]nonane-2,4,9-trione (16) to an unprecedented highly functionalized bicyclo[3.3.0]octane system (17), induced by an intramolecular Michael addition, is presented. This novel framework was found to be similarly active to hyperforin (1), against PC-3 cell lines. A mechanistic study was examined in detail, proposing a number of cascade transformations. Also, reactivity of the Δ(7,10)-double bond was examined under several conditions to explain the above results.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Floroglucinol
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Compostos Bicíclicos com Pontes
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Alcanos
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Octanos
Idioma:
En
Ano de publicação:
2013
Tipo de documento:
Article