Simple enantioselective approach to synthetic limonoids.
J Am Chem Soc
; 130(21): 6720-1, 2008 May 28.
Article
en En
| MEDLINE
| ID: mdl-18444655
ABSTRACT
An enantioselective and short approach to the synthesis of limonoids has been applied successfully to the simplest limonoid, 2. The carbon atoms of the tetracyclic framework were assembled in a single operation from the acylsilane 3 and the acetylenic sulfone 4 to form the chiral epoxide 5. Successive cationic and free-radical cyclizations starting with 5 generated the tetracyclic intermediates 9a, which was transformed into limonoid 2 by a sequence consisting of (1) oxidative cleavage of the exocyclic double bond, (2) stereoselective alpha-methylation, (3) furyl attachment, and (4) introduction of a 16-keto function.
Texto completo:
1
Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Limoninas
Idioma:
En
Revista:
J Am Chem Soc
Año:
2008
Tipo del documento:
Article
País de afiliación:
Estados Unidos