The First Synthesis of Pentadecyl 6-Hydroxydodecanoate a Novel Compound Isolated from the Leaves of Artabotrys odoratissimus

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.

Key words

pentadecyl 6-hydroxydodecanoate - ring cleavage - α-nitrocyclohexanone - nitroaldol reaction - Nef reaction

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