The absolute configuration determination of naturally occurring diacetylenic spiroacetal enol ethers from Artemisia lactiflora |
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Authors: | Liang MaFan Ge Chun-Ping TangChang-Qiang Ke Xi-Qiang LiAndreas Althammer Yang Ye |
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Institution: | State Key Laboratory of Drug Research and Department of Natural Products Chemistry, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu-Chong-Zhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, PR China |
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Abstract: | Six new naturally occurring diacetylenic spiroacetal enol ethers, Lactiflodiynes A-F (1-6), together with five known congeners (7-11), were isolated from the whole plant of Artemisia lactiflora (Compositae). The structures were elucidated by extensive spectroscopic methods, X-ray crystallography, chemical transformations, and CD. The absolute configuration of Lactiflodiyne A (1) was determined to be 2R, 5S, 6S, and 7R by an X-ray crystallographic diffraction experiment using Mo Kα radiation with the absolute parameter of 0.01(8). In combination with CD, the absolute configurations of compounds 2-11 were confirmed by chemical transformations using 1 as the starting material. |
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Keywords: | Artemisia lactiflora Diacetylenic spiroacetal enol ethers Absolute configuration Chemical transformation X-ray crystallography Circular dichroism |
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