Stereocontrolled synthesis of dafachronic acid A, the ligand for the DAF-12 nuclear receptor of Caenorhabditis elegans

被引:34
作者
Giroux, Simon [1 ]
Corey, E. J. [1 ]
机构
[1] Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA 02138 USA
关键词
D O I
10.1021/ja074306i
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient synthetic route to the DAF-12 nuclear receptor ligand of C. elegans, dafachronic acid, is described that starts with the abundant plant sterol beta-stigmasterol and proceeds in 37% overall yield. The synthesis establishes the structure of this rare nematode hormone.
引用
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页码:9866 / +
页数:3
相关论文
共 17 条
[1]   Physiology - The tick-tock of aging? [J].
Antebi, A .
SCIENCE, 2005, 310 (5756) :1911-1913
[2]  
ANTEBI A, ONLINE RESOURCE C EL
[3]  
BRENNER S, NOBEL LECT
[4]   TOTAL SYNTHESIS OF GLYCINOECLEPIN-A [J].
COREY, EJ ;
HOUPIS, IN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (24) :8997-8998
[5]  
COREY EJ, 1973, TETRAHEDRON LETT, V14, P4425
[6]  
EUMURA T, 1996, J ORG CHEM, V61, P5510
[7]  
FUKUZAWA A, 1985, J CHEM SOC CHEM COMM, P748, DOI 10.1039/c39850000748
[8]   Hormonal signals produced by DAF-9/cytochrome P450 regulate C-elegans dauer diapause in response to environmental cues [J].
Gerisch, B ;
Antebi, A .
DEVELOPMENT, 2004, 131 (08) :1765-1776
[9]   A bile acid-like steroid modulates Caenorhabditis elegans lifespan through nuclear receptor signaling [J].
Gerisch, Birgit ;
Rottiers, Veerle ;
Li, Dongling ;
Motola, Daniel L. ;
Cummins, Carolyn L. ;
Lehrach, Hans ;
Mangelsdorf, David J. ;
Antebi, Adam .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2007, 104 (12) :5014-5019
[10]   SYNTHETIC MICROBIAL CHEMISTRY .19. THE SYNTHESIS OF (-)-SIRENIN, SPERM ATTRACTANT OF THE WATER MOLD ALLOMYCES-MACROGYNUS [J].
KITAHARA, T ;
HORIGUCHI, A ;
MORI, K .
TETRAHEDRON, 1988, 44 (15) :4713-4720