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

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Abstract

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.

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Journal

Journal ID (iso-abbrev): Org. Lett.

Title: Organic letters

Publisher: American Chemical Society (ACS)

ISSN (Electronic): 1523-7052

ISSN (Print): 1523-7052

Publication date (Electronic): May 17 2017

Affiliations

[1 ] State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University , 222 Tianshui Nanlu, Lanzhou 730000, China.

[2 ] College of Chemistry and Chemical Engineering, Liaocheng University , Liaocheng 252059, China.

[3 ] Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) , Tianjin 300071, China.

Article

DOI: 10.1021/acs.orglett.7b01202

PubMed ID: 28514154

SO-VID: 7df3346a-df3c-4a7d-98cf-aa6d2a068102

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