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
收藏
页码:9866 / +
页数:3
相关论文
共 17 条
[11]   ISOLATION OF A NATURAL HATCHING STIMULUS, GLYCINOECLEPIN-A, FOR THE SOYBEAN CYST NEMATODE [J].
MASAMUNE, T ;
ANETAI, M ;
TAKASUGI, M ;
KATSUI, N .
NATURE, 1982, 297 (5866) :495-496
[12]   Identification of ligands for DAF-12 that govern Dauer formation and reproduction in C. elegans [J].
Motola, DL ;
Cummins, CL ;
Rottiers, V ;
Sharma, KK ;
Li, TT ;
Li, Y ;
Suino-Powell, K ;
Xu, HE ;
Auchus, RJ ;
Antebi, A ;
Mangelsdorf, DJ .
CELL, 2006, 124 (06) :1209-1223
[13]   ASYMMETRIC HYDROGENATION OF UNSATURATED CARBOXYLIC-ACIDS CATALYZED BY BINAP-RUTHENIUM(II) COMPLEXES [J].
OHTA, T ;
TAKAYA, H ;
KITAMURA, M ;
NAGAI, K ;
NOYORI, R .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (14) :3174-3176
[14]   ALLYLIC OXIDATION WITH 3,5-DIMETHYLPYRAZOLE - CHROMIUM TRIOXIDE COMPLEX - STEROIDAL DELTA-5-7-KETONES [J].
SALMOND, WG ;
BARTA, MA ;
HAVENS, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (10) :2057-2059
[15]  
SALMOND WG, 1977, TETRAHEDRON LETT, V18, P1695
[16]   SOLVOLYSIS OF STIGMASTERYL TOSYLATE [J].
STEELE, JA ;
MOSETTIG, E .
JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (02) :571-&
[17]   THE THERMAL, ALIPHATIC CLAISEN REARRANGEMENT [J].
ZIEGLER, FE .
CHEMICAL REVIEWS, 1988, 88 (08) :1423-1452