Enantioselective synthesis of heliannuol E; Structural consideration of natural molecule

被引:39
作者
Doi, F [1 ]
Ogamino, T [1 ]
Sugai, T [1 ]
Nishiyama, S [1 ]
机构
[1] Keio Univ, Fac Sci & Technol, Dept Chem, Kohoku Ku, Yokohama, Kanagawa 2238522, Japan
关键词
heliannuol E; Helianthus annuus L. cv. SH-222; allelopathy; phenolic oxidation; ring expansion; spirodienone;
D O I
10.1016/S0040-4039(03)01094-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Heliannuol E 1, isolated from Helianthus annuus L. cv. SH-222, was successfully synthesized in both optically active forms. by novel ring-expansion reaction of the corresponding spirodienone derivatives 8 and 17, which were produced from 7 and 16 under anodic oxidation conditions. The absolute structure of the natural product was determined to have R-configuration at the benzylic position. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4877 / 4880
页数:4
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