Total Synthesis and Determination of the Absolute Configuration of (-)-Idesolide

被引：22

作者：

Yamakoshi, Hiroyuki ^{[1
]}

Shibuya, Masatoshi ^{[1
]}

Tomizawa, Masaki ^{[1
]}

Osada, Yuji ^{[1
]}

Kanoh, Naoki ^{[1
]}

Iwabuchi, Yoshiharu ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Dept Organ Chem, Sendai, Miyagi 9808578, Japan

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 05期

关键词：

ALKALOIDS; ALCOHOLS; DIMER;

D O I：

10.1021/ol9029676

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of (-)-idesolide was achieved via organocatalytic, enantioselective oxidative kinetic resolution (OKR) using (1S,4S)-4-Bn-1-Bu-AZADOH- and AZADO-catalyzed dimerization of (S)-(-)-methyl 1-hydroxy-6-oxo-2-cyclohexenecarboxylate. The absolute configuration of (-)-idesolide is determined to be 2R,2'S,3aS,7aR.

引用

页码：980 / 983

页数：4

共 50 条

[31] Total synthesis and determination of the absolute configuration of a natural analgesic: crotonine
Yang Y.
Natural Products and Bioprospecting, 2013, 3 (6) : 288 - 294
[32] The first total synthesis of putaminoxin and determination of its absolute configuration
Sabitha, Gowravaram
Yadagiri, K.
Swapna, R.
Yadav, J. S.
TETRAHEDRON LETTERS, 2009, 50 (38) : 5417 - 5419
[33] TOTAL SYNTHESIS OF NATURAL (-)-ECHINOSPORIN - DETERMINATION OF THE ABSOLUTE-CONFIGURATION
SMITH, AB
SULIKOWSKI, GA
FUJIMOTO, K
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (20) : 8039 - 8041
[34] Enantioselective total synthesis of (+)-gelsemine: Determination of its absolute configuration
Yokoshima, Satoshi
Tokuyama, Hidetoshi
Fukuyama, Tohru
Angewandte Chemie (International Edition in English), 2000, 39 (22): : 4073 - 4075
[35] Enantioselective Total Synthesis of (+)-Steenkrotin A and Determination of Its Absolute Configuration
Pan, Saiyong
Gao, Beiling
Hu, Jialei
Xuan, Jun
Xie, Hujun
Ding, Hanfeng
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (03) : 959 - 970
[36] Enantioselective total synthesis of (+)-gelsemine: Determination of its absolute configuration
Yokoshima, S
Tokuyama, H
Fukuyama, T
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2000, 39 (22) : 4073 - 4075
[37] An enantioselective total synthesis of (+)- and (-)-saudin. Determination of the absolute configuration
Boeckman, RK
Ferreira, MDR
Mitchell, LH
Shao, PC
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (02) : 190 - 191
[38] Asymmetric Total Synthesis of Gracilamine and Determination of Its Absolute Configuration
Zuo, Xiao-Dong
Guo, Shu-Min
Yang, Rui
Xie, Jian-Hua
Zhou, Qi-Lin
ORGANIC LETTERS, 2017, 19 (19) : 5240 - 5243
[39] Studies culminating in the total synthesis and determination of the absolute configuration of (-)-saudin
Boeckman, Robert K., Jr.
del Rosario Ferreira, Maria Rico
Mitchell, Lorna H.
Shao, Pengcheng
Neeb, Michael J.
Fang, Yue
TETRAHEDRON, 2011, 67 (51) : 9787 - 9808
[40] The first total synthesis and determination of the absolute configuration of chapecoderin A, B and C
Hagiwara, H
Takeuchi, F
Nozawa, M
Hoshi, T
Suzuki, T
TETRAHEDRON, 2004, 60 (09) : 1983 - 1989

← 1 2 3 4 5 →