Biomimetic Dehydrogenative Diels-Alder Cycloadditions: Total Syntheses of Brosimones A and B

被引:60
|
作者
Qi, Chao [1 ,2 ]
Cong, Huan [1 ,2 ]
Cahill, Katharine J. [3 ]
Muller, Peter [4 ]
Johnson, Richard P. [3 ]
Porco, John A., Jr. [1 ,2 ]
机构
[1] Boston Univ, Dept Chem, Boston, MA 02215 USA
[2] Boston Univ, Ctr Chem Methodol & Lib Dev CMLD BU, Boston, MA 02215 USA
[3] Univ New Hampshire, Dept Chem, Durham, NH 03824 USA
[4] MIT, Dept Chem, Cambridge, MA 02139 USA
基金
美国国家科学基金会;
关键词
brosimone; dehydrogenative cycloaddition; Diels-Alder cycloaddition; nanoparticle catalysts; natural product synthesis; OBLONGIFOLIA; CONSTITUENTS; CHEMISTRY; ADDUCT;
D O I
10.1002/anie.201302847
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Passing (H2) gas: Concise syntheses of the natural products brosimones A and B have been achieved using sequential dehydrogenative Diels-Alder (DHDA) cycloadditions. The syntheses employ either Pt/C-cyclopentene or DDQ to effect dehydrogenation of prenylchalcone substrates in combination with silver nanoparticles to promote subsequent Diels-Alder cycloadditions. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:8345 / 8348
页数:4
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