Stereoselective and efficient synthesis of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol.
Org Lett
; 7(26): 5917-20, 2005 Dec 22.
Article
em En
| MEDLINE
| ID: mdl-16354099
ABSTRACT
[reaction see text] Two short and efficient synthesis routes have been developed for bis-THF-alcohol 2, a key building block of the investigational HIV protease inhibitor TMC114 (1). Using S-2,3-O-isopropylideneglyceraldehyde (4) as the source of chirality, both routes are based on a diastereoselective Michael addition of nitromethane to give predominantly the syn congeners 6 followed by a Nef oxidation and cyclization to afford lactone acetals 8, which are reduced and cyclized to give 2.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Sulfonamidas
/
Inibidores da Protease de HIV
/
Furanos
Idioma:
En
Ano de publicação:
2005
Tipo de documento:
Article