Synthetic studies toward GKK1032s, novel antibiotic antitumor agents: enantioselective synthesis of the fully elaborated tricyclic core via an intramolecular Diels-Alder cycloaddition.
J Org Chem
; 71(18): 6942-51, 2006 Sep 01.
Article
en En
| MEDLINE
| ID: mdl-16930048
ABSTRACT
An enantioselective synthesis of the fully elaborated tricyclic decahydrofluorene core (ABC-ring system) of GKK1032s, novel antimicrobial and antitumor agents, has been accomplished for the first time by employing a highly diastereoselective intramolecular Diels-Alder (IMDA) reaction. The key substrate for the IMDA reaction was efficiently prepared through (i) an intermolecular Diels-Alder reaction between a siloxydiene and an optically active enone derived from D-mannitol to construct the appropriately functionalized C-ring and (ii) CuCl-promoted Stille coupling of an (E)-vinyl iodide and a vinylstannane to install the requisite triene side chain as the crucial steps.
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Colección:
01-internacional
Banco de datos:
MEDLINE
Asunto principal:
Química Orgánica
/
Compuestos Heterocíclicos de 4 o más Anillos
/
Antibióticos Antineoplásicos
Idioma:
En
Revista:
J Org Chem
Año:
2006
Tipo del documento:
Article
País de afiliación:
Japón