Literature DB >> 27934032

Total Syntheses of Aflavazole and 14-Hydroxyaflavinine.

Hailong Li1, Qifeng Chen1, Zhaohong Lu1, Ang Li1.   

Abstract

The first total syntheses of aflavazole (6) and 14-hydroxyaflavinine (8), two sterically congested indole diterpenoids, were accomplished. AlI3-promoted alkyne Prins cyclization was exploited to construct their key structural motifs. An electrocyclization-aromatization sequence assembled the pentasubstituted arene of 6, and a Stille-Migita coupling furnished the tetrasubstituted olefin of 8. The benzylic and allylic C-O bonds were reductively cleaved at the late stage of the syntheses, respectively.

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Year:  2016        PMID: 27934032     DOI: 10.1021/jacs.6b10880

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  6 in total

1.  Total Synthesis of (-)-Nodulisporic Acids D, C, and B: Evolution of a Unified Synthetic Strategy.

Authors:  Yike Zou; Xiangqin Li; Yun Yang; Simon Berritt; Jason Melvin; Stephen Gonzales; Matthew Spafford; Amos B Smith
Journal:  J Am Chem Soc       Date:  2018-07-20       Impact factor: 15.419

2.  Total Synthesis of (+)-Granatumine A and Related Bislactone Limonoid Alkaloids via a Pyran to Pyridine Interconversion.

Authors:  Alexander W Schuppe; Yizhou Zhao; Yannan Liu; Timothy R Newhouse
Journal:  J Am Chem Soc       Date:  2019-06-03       Impact factor: 15.419

3.  Transformation of Organostannanes Based on Photocleavage of C-Sn Bond via Single Electron Transfer Process.

Authors:  Han Li; Ruiwen Jin; Yawei Li; Aishun Ding; Xinqi Hao; Hao Guo
Journal:  Sci Rep       Date:  2017-11-29       Impact factor: 4.379

4.  Direct access to multi-functionalized benzenes via [4 + 2] annulation of α-cyano-β-methylenones and α,β-unsaturated aldehydes.

Authors:  Qianfa Jia; Yunfei Lan; Xin Ye; Yinhe Lin; Qiao Ren
Journal:  RSC Adv       Date:  2020-08-06       Impact factor: 4.036

5.  The Enantioselective Synthesis of Eburnamonine, Eucophylline, and 16'-epi-Leucophyllidine.

Authors:  Christopher E Reimann; Aurapat Ngamnithiporn; Kohei Hayashida; Daisuke Saito; Katerina M Korch; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2021-07-06       Impact factor: 16.823

Review 6.  Applications of ultrasound in total synthesis of bioactive natural products: A promising green tool.

Authors:  Sasadhar Majhi
Journal:  Ultrason Sonochem       Date:  2021-07-18       Impact factor: 7.491

  6 in total

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