Enantioselective total synthesis of (-)-acylfulvene and (-)-irofulven.
J Org Chem
; 74(24): 9292-304, 2009 Dec 18.
Article
em En
| MEDLINE
| ID: mdl-19938810
ABSTRACT
We report our full account of the enantioselective total synthesis of (-)-acylfulvene (1) and (-)-irofulven (2), which features metathesis reactions for the rapid assembly of the molecular framework of these antitumor agents. We discuss (1) the application of an Evans Cu-catalyzed aldol addition reaction using a strained cyclopropyl ketenethioacetal, (2) an efficient enyne ring-closing metathesis cascade reaction in a challenging setting, (3) the reagent IPNBSH for a late-stage reductive allylic transposition reaction, and (4) the final RCM/dehydrogenation sequence for the formation of (-)-acylfulvene (1) and (-)-irofulven (2).
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Sesquiterpenos
/
Antineoplásicos
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2009
Tipo de documento:
Article
País de afiliação:
Estados Unidos