Conjugate addition-dipolar cycloaddition cascade for the synthesis of benzo[a]quinolizine and indolo[a]quinolizine scaffolds: application to the total synthesis of (+/-)-yohimbenone.
J Org Chem
; 74(9): 3491-9, 2009 May 01.
Article
in En
| MEDLINE
| ID: mdl-19338296
ABSTRACT
A highly efficient total synthesis of (+/-)-yohimbenone and a formal synthesis of (+/-)-emetine is described. The key element of the synthesis consists of a conjugate addition-dipolar cycloaddition of 2,3-bis(phenylsulfonyl)-1,3-butadiene with an appropriate oxime. The resulting cycloadducts are cleaved reductively to provide azapolycyclic scaffolds with strategically placed functionality for further manipulation to the target compounds.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Quinolizines
/
Heterocyclic Compounds, 4 or More Rings
/
Indoles
Language:
En
Journal:
J Org Chem
Year:
2009
Type:
Article
Affiliation country:
United States