Synthesis and Characterization of 12-Acyloxyimino-1,15-pentadecanolides

Abstract

Abstract: By the addition with acraldehyde, ring-enlargement and Nef reaction, 12-acyloximino-1, 15-pentadecanolides were synthesized from α-nitro-cyclododecanone. cis- and trans-isomers of 12-acyloxyimi-no-l,15-pentadecanolides were obtained by oximation, O-acylation and silica gel column chromatography separation, respectively. The structure of all the title compounds were confirmed by IR, ¹HNMR and elementary analysis. Their configurations and conformations were determined by the crystal X-ray analysis of a representative compound and ¹HNMR. The results show that the oximation of 12-oxo-l,15-pentade-canolide displays low selectivity for cis- and trans- isomers and the preferred conformation of the ring skeleton is[23434], with the carbonyl group and oximido group present in the two different corner-carbon positions, respectively.

Key words: 12-Oximido-1,15-pentadecanolide, 12-Acyloxyimino-1,15-pentadecanolide, Synthesis

CLC Number:

O621

TrendMD:

ZHANG Jian-Jun, DONG Yan-Hong, LIANG Xiao-Mei, WANG Dao-Quan. Synthesis and Characterization of 12-Acyloxyimino-1,15-pentadecanolides[J]. Chem. J. Chinese Universities, 2003, 24(9): 1604.

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Synthesis and Characterization of 12-Acyloxyimino-1,15-pentadecanolides

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