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

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.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11581/242128
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