Enantioselective photocycloaddition mediated by chiral Bronsted acids: Asymmetric synthesis of the rocaglamides

被引：104

作者：

Gerard, Baudouin

Sangji, Sheharbano

O'Leary, Daniel J.

Porco, John A., Jr.

机构：

[1] Boston Univ, Dept Chem, Boston, MA 02215 USA

[2] Boston Univ, Ctr Chem Methodol & Lib Dev, Boston, MA 02215 USA

[3] Pomona Coll, Dept Chem, Claremont, CA 91711 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 24期

关键词：

D O I：

10.1021/ja062621j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantioselective syntheses of methyl rocaglate and the related natural products rocaglamide and rocaglaol are outlined. The approach involves enantioselective [3 + 2] photocycloaddition promoted by chiral Brønsted acids (TADDOLs) to afford an aglain precursor followed by a ketol shift/reduction sequence to the rocaglate core. Copyright © 2006 American Chemical Society.

引用

收藏

页码：7754 / 7755

页数：2

相关论文

共 28 条

[1]

Adembri G, 2003, J CHEM RES, P126

[2] Proton transfer in 3-hydroxyflavone studied by high-resolution 10 K laser-excited Shpol'skii spectroscopy [J].

Bader, AN ;

Ariese, F ;

Gooijer, C .

JOURNAL OF PHYSICAL CHEMISTRY A, 2002, 106 (12) :2844-2849

[3] Catalytic enantioselective reactions driven by photoinduced electron transfer [J].

Bauer, A ;

Westkämper, F ;

Grimme, S ;

Bach, T .

NATURE, 2005, 436 (7054) :1139-1140

[4]

BECK AK, 1991, CHIMIA, V45, P238

[5]

Bhasker V., 2005, ORG LETT, V7, P5657

[6] A highly efficient synthesis of rocaglaols by a novel α-arylation of ketones [J].

Diedrichs, N ;

Ragot, JP ;

Thede, K .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (09) :1731-1735

[7] A synthetic derivative of the natural product rocaglaol is a potent inhibitor of cytokine-mediated signaling and shows neuroprotective activity in vitro and in animal models of Parkinson's disease and traumatic brain injury [J].

Fahrig, T ;

Gerlach, I ;

Horváth, E .

MOLECULAR PHARMACOLOGY, 2005, 67 (05) :1544-1555

[8] A biomimetic approach to the rocaglamides employing photogeneration of oxidopyryliums derived from 3-hydroxyflavones [J].

Gerard, B ;

Jones, G ;

Porco, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (42) :13620-13621

[9]

GREENE AE, 1976, TETRAHEDRON LETT, P2707

[10] Highly enantioselective Diels-Alder reaction of a photochemically generated o-quinodimethane with olefins [J].

Grosch, B ;

Orlebar, CN ;

Herdtweck, E ;

Massa, W ;

Bach, T .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (31) :3693-3696