Diastereoselective Synthesis of β-Piperonyl-γ-Butyrolactones from Morita-Baylis-Hillman Adducts. Highly Efficient Synthesis of (±)-Yatein, (±)-Podorhizol and (±)-epi-Podorhizol

被引：9
|
作者：
Trazzi, Giordano [1 ]
Andre, Marcelo Fabiano [1 ]
Coelho, Fernando [1 ]
机构：
[1] Univ Estadual Campinas, Inst Quim, BR-13083970 Campinas, SP, Brazil
来源：
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY | 2010年 / 21卷 / 12期
基金：
巴西圣保罗研究基金会;
关键词：
Morita-Baylis-Hillman; lignans; diastereoselectivity; ELECTROSPRAY-IONIZATION MASS; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; LIGNAN LACTONES; DIBENZYLBUTYROLACTONE LIGNANS; ENANTIOSELECTIVE SYNTHESIS; BIOLOGICAL-ACTIVITIES; ALTERNATIVE APPROACH; SODIUM-BOROHYDRIDE; ORGANIC-SYNTHESIS;
D O I：
10.1590/S0103-50532010001200021
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Starting from a Morita-Baylis-Hillman adduct we describe a simple and very efficient method for the diastereoselective preparation of hydroxylated beta-piperonyl-gamma-butyrolactones. To exemplify the efficiency of this approach we also describe a highly efficient synthesis for the biologically active lignans (+/-)-yatein, (+/-)-podorhizol and (+/-)-epi-podorhizol.
引用
收藏
页码：2327 / 2339
页数：13
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