Nitroalkanes as central reagents in the synthesis of spiroketals.
Nitroalkanes can be profitably employed as carbanionic precursors for the assembly of dihydroxy ketone frameworks, suitable for the preparation of spiroketals. The carbon-carbon bond formation is carried out exploiting nitroaldol and Michael reactions, while the nitro to carbonyl conversion (Nef reaction) ensures the correct introduction of the keto group. Several spiroketal systems endowed with considerable biological activity can be prepared using this synthetic strategy.
Ballini
Roberto
R
Dipartimento di Scienze Chimiche, Università di Camerino, via S.Agostino, 1, I-62032 Camerino, Italy. roberto.ballini@unicam.it
Petrini
Marino
M
Rosini
Goffredo
G
D000473:Alkanes / Q000138:chemical synthesis / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D009574:Nitro Compounds / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D000473:Alkanes; D005663:Furans; D007202:Indicators and Reagents; D009574:Nitro Compounds; D013141:Spiro Compounds; C520774:spiroketal; C012867:decane; C017573:nonane