Enantio- and diastereocontrolled synthesis of an angular triquinane sesquiterpene (+)-arnicenone

被引:27
作者
Iura, Y [1 ]
Sugahara, T [1 ]
Ogasawara, K [1 ]
机构
[1] Tohoku Univ, Inst Pharmaceut, Sendai, Miyagi 9808578, Japan
关键词
D O I
10.1021/ol006922o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] (+)-Arnicenone, a sesquiterpene of an angular triquinane isolated from Arnica plants, has been synthesized for the first time in an enantiocontrolled manner from a synthetic equivalent of chiral 2-hydroxymethylcyclopentadienone to determine the absolute configuration of the natural product as 1R,3aR,5aS,8aR.
引用
收藏
页码:291 / 293
页数:3
相关论文
共 19 条
[1]   SELECTIVE REDUCTIONS .26. LITHIUM TRIETHYLBOROHYDRIDE AS AN EXCEPTIONALLY POWERFUL AND SELECTIVE REDUCING AGENT IN ORGANIC-SYNTHESIS - EXPLORATION OF THE REACTIONS WITH SELECTED ORGANIC-COMPOUNDS CONTAINING REPRESENTATIVE FUNCTIONAL-GROUPS [J].
BROWN, HC ;
KIM, SC ;
KRISHNAMURTHY, S .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (01) :1-12
[2]   Recent advances in the Pauson-Khand reaction and related [2+2+1] cycloadditions [J].
Brummond, KM ;
Kent, JL .
TETRAHEDRON, 2000, 56 (21) :3263-3283
[3]   STEREOSPECIFIC REARRANGEMENTS IN TRICYCLOPENTANOID SESQUITERPENES - THE ABSOLUTE-CONFIGURATION OF (-)-ISOCOMENE, (-)-BETA-ISOCOMENE, AND (-)-SILPHINENE [J].
FITJER, L ;
MONZOOLTRA, H .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (23) :6171-6173
[4]  
Huang M., 1949, J AM CHEM SOC, V71, P3301
[5]   Oxidative resolution of 2-cyclopentenols by the asymmetric hydrogen transfer protocol [J].
Iura, Y ;
Sugahara, T ;
Ogasawara, K .
TETRAHEDRON LETTERS, 1999, 40 (31) :5735-5738
[6]  
KAMIKUBO T, 1995, CHEM COMMUN, P1951
[7]  
Kanada RM, 2000, SYNLETT, P1019
[8]   Asymmetric hydrogen transfer protocol for enantiocontrolled synthesis of (-)-chokol G [J].
Kanada, RM ;
Taniguchi, T ;
Ogasawara, K .
CHEMICAL COMMUNICATIONS, 1998, (16) :1755-1756
[9]  
Kanada RM, 2000, TETRAHEDRON LETT, V41, P3631
[10]  
KEUM Y, 1993, ORGANOMETALLICS, V12, P220