Asymmetric formal synthesis of (+)-cycloclavine

被引：12

作者：

Chen, Jin-Quan ^{[1
]}

Song, Le-Le ^{[1
]}

Li, Feng-Xing ^{[1
]}

Shi, Zi-Fa ^{[1
]}

Cao, Xiao-Ping ^{[1
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Coll Chem & Chem Engn, Lanzhou 730000, Gansu, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2017年 / 53卷 / 96期

基金：

中国国家自然科学基金;

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; VINYLOGOUS MANNICH REACTIONS; TERT-BUTANESULFINYL IMINES; ERGOT ALKALOIDS; SELECTIVE SYNTHESIS; CLAVINE ALKALOIDS; ALLENYL ALCOHOLS; (+/-)-CYCLOCLAVINE; LACTONES; AMINES;

D O I：

10.1039/c7cc08044a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The asymmetric synthesis of Szantay's amine (+)-2, the pivotal precursor for direct access to (+)-cycloclavine (1), is described for the first time in eleven steps with 19.7% overall yield from the commercially available 4-bromoindole. The strategy features an asymmetric induction by Ellman's sulfinimine and rhodium-catalysed isomerization of the C=C bond.

引用

页码：12902 / 12905

页数：4

共 50 条

[1] Formal Synthesis of (±)-Cycloclavine
Wang, Wei
Lu, Jia-Tian
Zhang, Hao-Li
Shi, Zi-Fa
Wen, Jing
Cao, Xiao-Ping
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (01): : 122 - 127
[2] Formal and total synthesis of (±)-cycloclavine
Jabre, Nitinkumar D.
Watanabe, Teruki
Brewer, Matthias
TETRAHEDRON LETTERS, 2014, 55 (01) : 197 - 199
[3] Catalytic asymmetric formal total syntheses of (+)- and (-)-cycloclavine
Chaudhuri, Saikat
Ghosh, Santanu
Bhunia, Subhajit
Bisai, Alakesh
CHEMICAL COMMUNICATIONS, 2018, 54 (08) : 940 - 943
[4] A Modular Formal Total Synthesis of (±)-Cycloclavine
Netz, Natalie
Opatz, Till
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (04): : 1723 - 1730
[5] Enantioselective Formal Synthesis of (+)-Cycloclavine and Total Synthesis of (+)-5-epi-Cycloclavine
Wang, Wei
Mi, Yang
Cao, Xiao-Ping
Shi, Zi-Fa
ORGANIC LETTERS, 2019, 21 (17) : 6603 - 6607
[6] Progress toward the asymmetric total synthesis of (+)-cycloclavine
Zhang, Yilin
McArdle, Ian
Soderberg, Bjorn
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
[7] Asymmetric Total Synthesis and Biological Evaluation of (+)-Cycloclavine
McCabe, Stephanie R.
Wipf, Peter
SYNTHESIS-STUTTGART, 2019, 51 (01): : 213 - 224
[8] Concise Synthesis of (-)-Cycloclavine and (-)-5-epi-Cycloclavine via Asymmetric C-C Activation
Deng, Lin
Chen, Mengqing
Dong, Guangbin
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (30) : 9652 - 9658
[9] Concise Synthesis of (-)-Cycloclavine and (-)-5- epi-Cycloclavine via Asymmetric C-C Activation
Dong, Guangbin (gbdong@uchicago.edu), 2018, American Chemical Society (140)
[10] Total Synthesis of (±)-Cycloclavine and (±)-5-epi-Cycloclavine
Petronijevic, Filip R.
Wipf, Peter
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (20) : 7704 - 7707

← 1 2 3 4 5 →