Determination of absolute configurations of carbinols of annonaceous acetogenins with 2-naphthylmethoxyacetic acid esters

被引:19
作者
Duret, P [1 ]
Waechter, AI [1 ]
Figadère, B [1 ]
Hocquemiller, R [1 ]
Cavé, A [1 ]
机构
[1] Univ Paris Sud, Fac Pharm, Lab Pharmacognosie, CNRS BIOCIS, F-92296 Chatenay Malabry, France
关键词
D O I
10.1021/jo980409v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Structural elucidation of absolute configurations of the stereogenic centers of acetogenins of Annonaceae was performed using the modified Mosher's method. Thus, by replacing MTPA (methoxytrifluoromethylphenylacetic acid) by 2-NMA (naphthylmethoxyacetic acid), we were able to determine the absolute configuration of the stereogenic centers of rolliniastatin-2 by simple analysis of the (1)H NMR spectra recorded at 400 MHz. Indeed, by comparing the differences of chemical shifts between the MTPA esters with those obtained with 8-NMA esters, we showed that we could take advantage of the long-range anisotropic effect of the naphthyl ring for the elucidation: of the unsymmetrical systems.
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页码:4717 / 4720
页数:4
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