The pentadecyl 6-hydroxydodecanoate 8, a new hydroxy ester isolated from leaves of Artabotrys odoratissima has been synthesized, for the first time, from α-nitrocyclohexanone 1, via (i) nucleophilic ring cleavage performed with 1-pentadecanol 2, (ii) nitroaldol reaction of the formed ω-nitro ester 3 with hexanal 4, (iii) dehydratation of the obtained nitroalkanol 5 to the conjugate nitroolefin 6, (iv) direct Nef conversion of the nitroalkene 6 to the keto ester 7, and (v) sodium borohydride reduction of the carbonyl functionality in order to convert the keto ester 7 into the target hydroxy ester 8.
The First Synthesis of Pentadecyl 6-Hydroxydodecanoate a Novel Compound Isolated from the Leaves of Artabotrys odoratissimus
BALLINI, Roberto;FIORINI, Dennis;PALMIERI, Alessandro
2003-01-01
Abstract
The pentadecyl 6-hydroxydodecanoate 8, a new hydroxy ester isolated from leaves of Artabotrys odoratissima has been synthesized, for the first time, from α-nitrocyclohexanone 1, via (i) nucleophilic ring cleavage performed with 1-pentadecanol 2, (ii) nitroaldol reaction of the formed ω-nitro ester 3 with hexanal 4, (iii) dehydratation of the obtained nitroalkanol 5 to the conjugate nitroolefin 6, (iv) direct Nef conversion of the nitroalkene 6 to the keto ester 7, and (v) sodium borohydride reduction of the carbonyl functionality in order to convert the keto ester 7 into the target hydroxy ester 8.File in questo prodotto:
Non ci sono file associati a questo prodotto.
I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
