Literature DB >> 21985106

β-Silyl styrene as a dienophile in the cycloaddition with 3,5-dibromo-2-pyrone for the total synthesis of (±)-pancratistatin.

Yong-Geun Jung1, Ho-Ung Kang, Hyun-Kyu Cho, Cheon-Gyu Cho.   

Abstract

A new synthetic route to (±)-pancratistatin was devised utilizing β-silyl styrene as a dienophile in the cycloaddition with 3,5-dibromo-2-pyrone. The TMS group incorporated in the cycloadduct permitted a facile elimination process for the eventual installation of the C(1)-OH function. Subsequent transformations including Curtius rearrangement and Bischler-Napieralski reactions completed the total synthesis of (±)-pancratistatin.
© 2011 American Chemical Society

Entities:  

Mesh：

Substances：

Year:  2011        PMID： 21985106     DOI： 10.1021/ol202525a

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  9 in total

1.  Total Synthesis of (+)-Pancratistatin by the Rh(III)-Catalyzed Addition of a Densely Functionalized Benzamide to a Sugar-Derived Nitroalkene.

Authors:  Tyler J Potter; Jonathan A Ellman
Journal:  Org Lett       Date:  2017-05-24       Impact factor: 6.005

2.  Enantioselective Synthesis of Isocarbostyril Alkaloids and Analogs Using Catalytic Dearomative Functionalization of Benzene.

Authors:  Tanner W Bingham; Lucas W Hernandez; Daniel G Olson; Riley L Svec; Paul J Hergenrother; David Sarlah
Journal:  J Am Chem Soc       Date:  2018-12-20       Impact factor: 15.419

3.  Short, enantioselective total synthesis of chatancin.

Authors:  Yu-Ming Zhao; Thomas J Maimone
Journal:  Angew Chem Int Ed Engl       Date:  2014-12-02       Impact factor: 15.336

4.  Synthesis of (+)-Pancratistatins via Catalytic Desymmetrization of Benzene.

Authors:  Lucas W Hernandez; Jola Pospech; Ulrich Klöckner; Tanner W Bingham; David Sarlah
Journal:  J Am Chem Soc       Date:  2017-10-25       Impact factor: 15.419

Review 5.  The Curtius rearrangement: mechanistic insight and recent applications in natural product syntheses.

Authors:  Arun K Ghosh; Anindya Sarkar; Margherita Brindisi
Journal:  Org Biomol Chem       Date:  2018-02-26       Impact factor: 3.876

Review 6.  Recent advances in the synthesis of 2-pyrones.

Authors:  Jong Seok Lee
Journal:  Mar Drugs       Date:  2015-03-23       Impact factor: 5.118

7.  Organocatalytic Asymmetric Synthesis of Dihydroisoquinolinones via a One-Pot Aza-Henry-Hemiaminalization-Oxidation Sequence.

Authors:  Robert Hahn; Ehsan Jafari; Gerhard Raabe; Dieter Enders
Journal:  Synthesis (Stuttg)       Date:  2015-02-01       Impact factor: 3.157

Review 8.  Assessment on facile Diels-Alder approach of α-pyrone and terpenoquinone for the expedient synthesis of various natural scaffolds.

Authors:  Aluru Rammohan; Albert F Khasanov; Dmitry S Kopchuk; Duvvuru Gunasekar; Grigory V Zyryanov; Oleg N Chupakhin
Journal:  Nat Prod Bioprospect       Date:  2022-03-31

9.  Short, enantioselective, gram-scale synthesis of (-)-zephyranthine.

Authors:  Yuxiang Zhao; Yanren Zhu; Guolan Ma; Qi Wei; Shaoxiong Yang; Xiaoyu Zeng; Hongbin Zhang; Jingbo Chen
Journal:  Chem Sci       Date:  2021-06-21       Impact factor: 9.825
  9 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.