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

Authors :
Roberto Ballini
Source :
Synthesis; Apr2003, Vol. 2003 Issue 5, p0665-0667, 3p
Publication Year :
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. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
00397881
Volume :
2003
Issue :
5
Database :
Complementary Index
Journal :
Synthesis
Publication Type :
Academic Journal
Accession number :
20238558
Full Text :
https://doi.org/10.1055/s-2003-38083