Enantioselective synthesis and absolute configuration assignment of gabosine O. Synthesis of (+)- and (-)-gabosine N and (+)- and (-)-epigabosines N and O.
[reaction: see text] A rational approach to the synthesis of gabosines and other related carba-sugars starting from a masked p-benzoquinone has been designed. The enantioselective acetylation of the hydroxyketal 2 provides a practical entry to either enantiomer of the target products. The strategy has been applied to the synthesis of (+)- and (-)-gabosines N and O and (+)- and (-)-epigabosines N and O. The absolute configuration of natural gabosine O has been established.
Alibés
Ramón
R
Universitat Autonoma de Barcelona, Departament de Química, 08193 Bellaterra, Spain.
Bayón
Pau
P
de March
Pedro
P
Figueredo
Marta
M
Font
Josep
J
Marjanet
Georgina
G
D016227:Benzoquinones / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003512:Cyclohexanones; D015394:Molecular Structure; D013237:Stereoisomerism
D016227:Benzoquinones; D003512:Cyclohexanones; C516134:gabosine N