Total Synthesis of (-)-Chanoclavine I and an Oxygen-Substituted Ergoline Derivative

被引：14

作者：

Lu, Jia-Tian

Shi, Zi-Fa

Cao, Xiao-Ping ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 15期

基金：

中国国家自然科学基金;

关键词：

ERGOT ALKALOIDS; INDOLE; STRATEGY;

D O I：

10.1021/acs.joc.7b00573

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and direct route to ergot alkaloid (-)-chanoclavine I (3) is described using the inexpensive compound (2R)-(+)-phenyloxirane (15) as a chiral pool in 13 steps with 17% overall yield. Key features of the synthesis include a palladium-catalyzed intramolecular aminoalkynylation of terminal olefin and a rhodium -catalyzed intramolecular [3 + 2] annulation. An oxygen-substituted ergoline derivative (-)-25 was also achieved by using the same strategy.

引用

收藏

页码：7774 / 7782

页数：9

相关论文

共 24 条

[1] Chains, Necklaces and Weaving Chain-link Grids from Self-Assembly Reactions [J].

Alvarino, Cristina ;

Simond, Damien ;

Lorente, Pau Moneva ;

Besnard, Celine ;

Williams, Alan F. .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (24) :8851-8858

[2] UBER HYDROAROMATISCHE EPOXYDE .2. [J].

HOPFF, H ;

HOFFMANN, H .

HELVETICA CHIMICA ACTA, 1957, 40 (06) :1585-1594

[3] A strategy for the total synthesis of dragmacidin E. Construction of the core ring system [J].

Huntley, Raymond J. ;

Funk, Raymond L. .

ORGANIC LETTERS, 2006, 8 (21) :4775-4778

[4] Discovery and Reconstitution of the Cycloclavine Biosynthetic Pathway-Enzymatic Formation of a Cyclopropyl Group [J].

Jakubczyk, Dorota ;

Caputi, Lorenzo ;

Hatsch, Anaelle ;

Nielsen, Curt A. F. ;

Diefenbacher, Melanie ;

Klein, Jens ;

Molt, Andrea ;

Schroeder, Hartwig ;

Cheng, Johnathan Z. ;

Naesby, Michael ;

O'Connor, Sarah E. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (17) :5117-5121

[5] Distal-Selective Hydroformylation using Scaffolding Catalysis [J].

Joe, Candice L. ;

Blaisdell, Thomas P. ;

Geoghan, Allison F. ;

Tan, Kian L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (24) :8556-8559

[6] SYNTHESIS OF (-)-CHANOCLAVINE-I [J].

KARDOS, N ;

GENET, JP .

TETRAHEDRON-ASYMMETRY, 1994, 5 (08) :1525-1533

[7] Novel Aza-analogous Ergoline Derived Scaffolds as Potent Serotonin 5-HT6 and Dopamine D2 Receptor Ligands [J].

Krogsgaard-Larsen, Niels ;

Jensen, Anders A. ;

Schroder, Tenna J. ;

Christoffersen, Claus. T. ;

Kehler, Jan .

JOURNAL OF MEDICINAL CHEMISTRY, 2014, 57 (13) :5823-5828

[8] Total Synthesis of (+)-Lysergic Acid [J].

Liu, Qiang ;

Zhang, Yu-An ;

Xu, Ping ;

Jia, Yanxing .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (21) :10885-10893

[9] Eight-Step Enantioselective Total Synthesis of (-)-Cycloclavine [J].

McCabe, Stephanie R. ;

Wipf, Peter .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (01) :324-327

[10] Intramolecular Dearomatizing [3+2] Annulation of α-Imino Carbenoids with Aryl Rings Furnishing 3,4-Fused Indole Skeletons [J].

Miura, Tomoya ;

Funakoshi, Yuuta ;

Murakami, Masahiro .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (06) :2272-2275