Au-Catalyzed [2+3] Annulation of Enamides with Propargyl Esters: Total Synthesis of Cephalotaxine and Cephalezomine H

被引：38

作者：

Ma, Xiao-Yan ^{[1
]}

An, Man-Tao ^{[1
]}

Zhao, Xian-He ^{[1
]}

Du, Ji-Yuan ^{[1
,3
]}

Deng, Yu-Hua ^{[1
]}

Zhang, Xiang-Zhi ^{[1
]}

Fan, Chun-An ^{[1
,2
]}

机构：

[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, 222 Tianshui Nanlu, Lanzhou 730000, Peoples R China

[2] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300071, Peoples R China

[3] Liaocheng Univ, Coll Chem & Chem Engn, Liaocheng 252059, Peoples R China

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 11期

关键词：

VERSATILE BUILDING-BLOCKS; FORMAL SYNTHESIS; GOLD CATALYSIS; NATURAL-PRODUCTS; CYCLIZATION; DERIVATIVES; ALKALOIDS; ACCESS;

D O I：

10.1021/acs.orglett.7b01202

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel Au-catalyzed [2 + 3] annulation reaction of enamides with propargyl esters has been developed, providing a new method for expeditious assembly of synthetically useful functionalized 1-azaspiro[4.4]nonane building blocks. Based on this key annulation, strategic installation of the pivotal azaspirocyclic core, followed by constructing the benzazepine unit via Witkop cyclization, led to the divergent total syntheses of cephalotaxine and cephalezomine H.

引用

页码：2965 / 2968

页数：4

共 50 条

[1] Natural products from Cephalotaxus sp.: chemical diversity and synthetic aspects [J].

Abdelkafi, Hajer ;

Nay, Bastien .

NATURAL PRODUCT REPORTS, 2012, 29 (08) :845-869

[2] CRYSTAL AND MOLECULAR-STRUCTURE OF CEPHALOTAXINE PARA-BROMOBENZOATE [J].

ARORA, SK ;

BATES, RB ;

GRADY, RA .

JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (09) :1269-1271

[3] Gold-catalysed reactions of diynes [J].

Asiri, Abdullah M. ;

Hashmi, A. Stephen K. .

CHEMICAL SOCIETY REVIEWS, 2016, 45 (16) :4471-4503

[4] TOTAL SYNTHESIS OF CEPHALOTAXINE [J].

AUERBACH, J ;

WEINREB, SM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (20) :7172-&

[5] Harnessing the Versatile Reactivity of Propargyl Alcohols and their Derivatives for Sustainable Complex Molecule Synthesis [J].

Ayers, Benjamin James ;

Chan, Philip Wai Hong .

SYNLETT, 2015, 26 (10) :1305-1339

[6] Enamide Derivatives: Versatile Building Blocks for Highly Functionalized α,β-Substituted Amines [J].

Bernadat, Guillaume ;

Masson, Geraldine .

SYNLETT, 2014, 25 (20) :2842-2867

[7] Enamides: valuable organic substrates [J].

Carbery, David R. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (19) :3455-3460

[8] Gold catalysis: up to six new bonds by a domino [3+2]/[2+1]/[2+1] cycloaddition [J].

Conyers, Ryan C. ;

Barnes, Charles L. ;

Gung, Benjamin W. .

TETRAHEDRON LETTERS, 2015, 56 (23) :3318-3321

[9] Enamide Derivatives: Versatile Building Blocks for Total Synthesis [J].

Courant, Thibaut ;

Dagousset, Guillaume ;

Masson, Geraldine .

SYNTHESIS-STUTTGART, 2015, 47 (13) :1799-1826

[10] Enamides and Related Functional Groups as Nucleophilic Components in Ring-Forming Processes Catalyzed by Electrophilic Metal Salts [J].

Dake, Gregory R. .

SYNLETT, 2012, (06) :814-824

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