Synthesis 2003(5): 0665-0667
DOI: 10.1055/s-2003-38083
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Roberto Ballini*, Maria Victoria Gil, Dennis Fiorini, Alessandro Palmieri
Dipartimento di Scienze Chimiche, Università, Via S. Agostino 1, 62032 Camerino (MC) - Italy
Fax: +39(0737)402297; e-Mail: roberto.ballini@unicam.it;
Further Information

Publication History

Received 15 January 2003
Publication Date:
21 March 2003 (online)

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.