Total synthesis of (+)-kopsihainanine A

被引：32

作者：

Mizutani, Masaya ^{[1
]}

Yasuda, Shigeo ^{[1
]}

Mukai, Chisato ^{[1
]}

机构：

[1] Kanazawa Univ, Grad Sch Med Sci, Div Pharmaceut Sci, Kanazawa, Ishikawa 9201192, Japan

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 43期

关键词：

CATALYZED DECARBOXYLATIVE ALLYLATION; DIHYDROXYLATION; CARBAZOLONES; ALKALOIDS; SYSTEM;

D O I：

10.1039/c4cc01843e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Total synthesis of (+)-kopsihainanine A was accomplished on the basis of (i) Stoltz's enantioselective decarboxylative asymmetric allylation and (ii) the proposed biogenetic pathway from the related alkaloid, kopsihainanine B. In addition, HPLC analysis of the synthetic (+)-kopsihainanine A confirmed its ee to be 99% with [alpha](D)(30) = 25.35.

引用

页码：5782 / 5785

页数：4

共 19 条

[1] Trifluoromethanesulfonic anhydride-4-(N,N-dimethylamino)pyridine as a reagent combination for effecting Bischler-Napieralski cyclisation under mild conditions: Application to total syntheses of the Amaryllidaceae alkaloids N-methylcrinasiadine, anhydrolycorinone, hippadine and oxoassoanine [J].

Banwell, MG ;

Bissett, BD ;

Busato, S ;

Cowden, CJ ;

Hockless, DCR ;

Holman, JW ;

Read, RW ;

Wu, AW .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (24) :2551-2553

[2]

Behenna DC, 2012, NAT CHEM, V4, P130, DOI [10.1038/nchem.1222, 10.1038/NCHEM.1222]

[3]

BLECHERT S, 1995, SYNTHESIS-STUTTGART, P592

[4] Kopsihainanines A and B, two unusual alkaloids from Kopsia hainanensis [J].

Chen, Jia ;

Chen, Jian-Jun ;

Yao, Xiaojun ;

Gao, Kun .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (15) :5334-5336

[5] Enantioselective Palladium-Catalyzed Decarboxylative Allylation of Carbazolones and Indolones: Formal Synthesis of (+)-KopsihainanineA [J].

Gartshore, Christopher J. ;

Lupton, David W. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (15) :4113-4116

[6] The Construction of All-Carbon Quaternary Stereocenters by Use of Pd-Catalyzed Asymmetric Allylic Alkylation Reactions in Total Synthesis [J].

Hong, Allen Y. ;

Stoltz, Brian M. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (14) :2745-2759

[7] Total Synthesis of (±)-Kopsihainanine A [J].

Jing, Peng ;

Yang, Zhen ;

Zhao, Changgui ;

Zheng, Huaiji ;

Fang, Bowen ;

Xie, Xingang ;

She, Xuegong .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (22) :6729-6732

[8] PREPARATION OF (S)-tert-ButylPHOX (Oxazole, 4-(1,1-dimethylethyl)-2-[2-(diphenylphosphino)phenyl]-4,5-dihydro-(4S)-) [J].

Krout, Michael R. ;

Mohr, Justin T. ;

Stoltz, Brian M. .

ORGANIC SYNTHESES, 2009, 86 :181-+

[9] Enantioselective Palladium-Catalyzed Decarboxylative Allylation of Carbazolones: Total Synthesis of (-)-Aspidospermidine and (+)-Kopsihainanine A [J].

Li, Zeqian ;

Zhang, Shaoxiong ;

Wu, Shoutao ;

Shen, Xiaolei ;

Zou, Liwei ;

Wang, Fengqun ;

Li, Xiang ;

Peng, Fangzhi ;

Zhang, Hongbin ;

Shao, Zhihui .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (15) :4117-4121

[10] Rapid synthesis of an electron-deficient t-BuPHOX ligand: cross-coupling of aryl bromides with secondary phosphine oxides [J].

McDougal, Nolan T. ;

Streuff, Jan ;

Mukherjee, Herschel ;

Virgil, Scott C. ;

Stoltz, Brian M. .

TETRAHEDRON LETTERS, 2010, 51 (42) :5550-5554

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