Oxabicyclo[3.2.1]octenes in organic synthesis: direct ring opening of oxabicyclo[3.2.1] ring systems with diisobutylaluminum hydride and a silyl ketene acetal--synthesis of the chiral C(19)-C(26) and C(27)-C(32) fragments of Scytophycin C.
Org Lett
; 4(2): 245-8, 2002 Jan 24.
Article
em En
| MEDLINE
| ID: mdl-11796061
ABSTRACT
[reaction see text] An efficient strategy for transforming meso-oxabicyclo[3.2.1]octenone 1 into optically active intermediates for macrolide synthesis has been developed. The direct bridgehead opening of optically active oxabicyclo[3.2.1]octene derivative 2 with hydride or a silyl ketene acetal utilizing the highly polar medium lithium perchlorate in diethyl ether resulted in highly functionalized cycloheptenones, which were transformed into the C(19)-C(26) and C(27)-C(32) fragments of Scytophycin C.
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01-internacional
Base de dados:
MEDLINE
Assunto principal:
Piranos
/
Compostos Bicíclicos Heterocíclicos com Pontes
/
Antineoplásicos
Idioma:
En
Ano de publicação:
2002
Tipo de documento:
Article