Design and synthesis of a library of tetracyclic hydroazulenoisoindoles.
J Comb Chem
; 11(3): 486-94, 2009.
Article
em En
| MEDLINE
| ID: mdl-19366169
ABSTRACT
Forty-four tetracyclic hydroazulenoisoindoles were synthesized via a tandem cyclopropanation/Cope rearrangement, followed by a Diels-Alder sequence from easily available five-membered cyclic cross-conjugated trienones. These trienones were obtained from two different routes depending upon whether R(1) and R(2) are alkyl or amino acid derived functional groups, via a rhodium(I)-catalyzed cycloisomerization reaction. To increase diversity, four maleimides and two 1,2,4-triazoline-3,5-diones were used as dienophiles in the Diels-Alder step. Several Diels-Alder adducts were further reacted under palladium-catalyzed hydrogenation conditions, leading to a diastereoselective reduction of the trisubstituted double bond. This library has demonstrated rapid access to a variety of structurally complex natural product-like compounds via stereochemical diversity and building block diversity approaches.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Técnicas de Química Combinatória
/
Bibliotecas de Moléculas Pequenas
Limite:
Animals
Idioma:
En
Ano de publicação:
2009
Tipo de documento:
Article