Total synthesis of (±)-jiadifenin, a non-peptidyl neurotrophic modulator

被引:59
作者
Cho, YS
Carcache, DA
Tian, Y
Li, YM
Danishefsky, SJ
机构
[1] Sloan Kettering Inst Canc Res, Bioorgan Chem Lab, New York, NY 10021 USA
[2] Sloan Kettering Inst Canc Res, Lab Biochem & Pharmacol, New York, NY 10021 USA
[3] Columbia Univ, Dept Chem, New York, NY 10027 USA
关键词
D O I
10.1021/ja045939p
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report the first total synthesis of jiadifenin (1), the establishment of a modality for its biological evaluation, and the discovery of apparently more potent neurotrophic activity in fully synthetic compound 17, an intermediate en route to 1. Copyright © 2004 American Chemical Society.
引用
收藏
页码:14358 / 14359
页数:2
相关论文
共 13 条
[1]   The total synthesis of (±)-merrilactone A [J].
Birman, VB ;
Danishefsky, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (10) :2080-2081
[2]   REACTIONS OF (+)-THUJONE AND (-)-ISOTHUJONE WITH FORMALDEHYDE [J].
BRIESKORN, CH ;
SCHWACK, W .
CHEMISCHE BERICHTE-RECUEIL, 1981, 114 (06) :1993-2000
[3]   ASYMMETRIC HYDROXYLATION OF ENOLATES WITH N-SULFONYLOXAZIRIDINES [J].
DAVIS, FA ;
CHEN, BC .
CHEMICAL REVIEWS, 1992, 92 (05) :919-934
[4]   BROMOMETRIC ASSAY OF CYCLOPENTOBARBITAL [J].
ERNST, L ;
GORLITZER, K ;
BOVENTER, K .
ARCHIV DER PHARMAZIE, 1990, 323 (06) :361-366
[5]   PREPARATION OF A USEFUL SYNTHON FOR CLERODANE ANTIFEEDANT SYNTHESIS [J].
GOLDSMITH, DJ ;
JOHN, TK ;
VANMIDDLESWORTH, F .
SYNTHETIC COMMUNICATIONS, 1980, 10 (07) :551-557
[6]   SYNTHESIS AND ASYMMETRIC REACTIVITY OF ENANTIOMERICALLY PURE CYCLOPENTADIENYLMETAL COMPLEXES DERIVED FROM THE CHIRAL POOL [J].
HALTERMAN, RL ;
VOLLHARDT, KPC .
ORGANOMETALLICS, 1988, 7 (04) :883-892
[7]   Pharmacology of neurotrophic factors [J].
Hefti, F .
ANNUAL REVIEW OF PHARMACOLOGY AND TOXICOLOGY, 1997, 37 :239-267
[8]   UBER STEROIDE .146. SYNTHESE VON 18-CARBOXY-STEROIDEN [J].
HEUSLER, K ;
UEBERWASSER, H ;
WIELAND, P ;
WETTSTEIN, A .
HELVETICA CHIMICA ACTA, 1957, 40 (03) :787-815
[9]   SESQUITERPENE LACTONES FROM THE PERICARPS OF ILLICIUM-MAJUS - 2-OXY DERIVATIVES OF NEOMAJUCIN AND 3,4-DEHYDROXYNEOMAJUCIN [J].
KOUNO, I ;
BABA, N ;
HASHIMOTO, M ;
KAWANO, N ;
TAKAHASHI, M ;
KANETO, H ;
YANG, CS .
CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (02) :422-425
[10]   Cyclohexenonic long-chain fatty alcohols as neuronal growth stimulators [J].
Luu, B ;
de Aguilar, JLG ;
Girlanda-Junges, C .
MOLECULES, 2000, 5 (12) :1439-1460