Literature DB >> 22149386

A tandem 1,3-H-shift-6π-electrocyclization-cyclic 2-amido-diene intramolecular Diels-Alder cycloaddition approach to BCD-Ring of atropurpuran.

Ryuji Hayashi1, Zhi-Xiong Ma, Richard P Hsung.   

Abstract

An approach toward the BCD-ring of atropurpuran via a sequence of allenic 1,3-H shift, 6π-electron pericyclic ring closure, and intramolecular Diels-Alder cycloaddition of cyclic 2-amidodiene is described.
© 2011 American Chemical Society

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Year:  2011        PMID： 22149386      PMCID： PMC3253247          DOI： 10.1021/ol203030a

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


  22 in total

Review 1.  C20-diterpenoid alkaloids.

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Authors:  Ryuji Hayashi; Mary C Walton; Richard P Hsung; John H Schwab; Xueliang Yu
Journal:  Org Lett       Date:  2010-11-19       Impact factor: 6.005

3.  A synthetic study of atropurpuran: construction of a pentacyclic framework by an intramolecular reverse-electron-demand Diels-Alder reaction.

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Review 4.  Diterpenoid and steroidal alkaloids.

Authors:  M I Choudhary
Journal:  Nat Prod Rep       Date:  1997-04       Impact factor: 13.423

Review 5.  Diterpenoid and steroidal alkaloids.

Authors:  M I Choudhary
Journal:  Nat Prod Rep       Date:  1995-08       Impact factor: 13.423

6.  Synthesis of allenamides by copper-catalyzed coupling of allenyl halides with amides, carbamates, and ureas.

Authors:  Barry M Trost; Dylan T Stiles
Journal:  Org Lett       Date:  2005-05-26       Impact factor: 6.005

7.  Efficient Baylis--Hillman reaction using stoichiometric base catalyst and an aqueous medium.

Authors:  C Yu; B Liu; L Hu
Journal:  J Org Chem       Date:  2001-08-10       Impact factor: 4.354

8.  The first regioselective alpha-deprotonation and functionalization of allenamides. An application in intramolecular Pauson-Khand-type cycloadditions.

Authors:  H Xiong; R P Hsung; L L Wei; C R Berry; J A Mulder; B Stockwell
Journal:  Org Lett       Date:  2000-09-07       Impact factor: 6.005

9.  Chemoselective cyclizations of divinyl ketones to cyclohexenones mediated by Lewis acid and base.

Authors:  Nabi A Magomedov; Piero L Ruggiero; Yuchen Tang
Journal:  Org Lett       Date:  2004-09-16       Impact factor: 6.005

10.  An efficient and practical entry to 2-amido-dienes and 3-amido-trienes from allenamides through stereoselective 1,3-hydrogen shifts.

Authors:  Ryuji Hayashi; John B Feltenberger; Andrew G Lohse; Mary C Walton; Richard P Hsung
Journal:  Beilstein J Org Chem       Date:  2011-04-07       Impact factor: 2.883
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  9 in total

1.  A highly stereoselective Diels-Alder cycloaddition of enones with chiral cyclic 2-amidodienes derived from allenamides.

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Journal:  Org Lett       Date:  2013-09-03       Impact factor: 6.005

2.  Facile Synthesis of 3-Amido-Dienynes via a Tandem α-Propargylation-Isomerization of Chiral Allenamides and their Applications in Diels-Alder Cycloadditions.

Authors:  Zhi-Xiong Ma; Li-Chao Fang; Richard P Hsung
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3.  α-Aryl-substituted allenamides in an imino-Nazarov cyclization cascade catalyzed by Au(I).

Authors:  Zhi-Xiong Ma; Shuzhong He; Wangze Song; Richard P Hsung
Journal:  Org Lett       Date:  2012-11-02       Impact factor: 6.005

Review 4.  Allenamides: a powerful and versatile building block in organic synthesis.

Authors:  Ting Lu; Zhenjie Lu; Zhi-Xiong Ma; Yu Zhang; Richard P Hsung
Journal:  Chem Rev       Date:  2013-04-04       Impact factor: 60.622

Review 5.  Retrosynthetic strategies and their impact on synthesis of arcutane natural products.

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Journal:  Chem Sci       Date:  2020-04-21       Impact factor: 9.825

Review 6.  Recent progress in transition-metal-free functionalization of allenamides.

Authors:  Xiaoxiao Li; Yongchun Liu; Na Ding; Xiaoju Tan; Zhigang Zhao
Journal:  RSC Adv       Date:  2020-10-06       Impact factor: 3.361

7.  Access to substituted cyclobutenes by tandem [3,3]-sigmatropic rearrangement/[2 + 2] cycloaddition of dipropargylphosphonates under Ag/Co relay catalysis.

Authors:  Qijian Ni; Xiaoxiao Song; Chin Wen Png; Yongliang Zhang; Yu Zhao
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8.  Stereoselective synthesis of isoquinuclidines through an aza-[4 + 2] cycloaddition of chiral cyclic 2-amidodienes.

Authors:  Li-Chao Fang; Richard P Hsung
Journal:  Org Lett       Date:  2014-03-12       Impact factor: 6.005

9.  Total synthesis of atropurpuran.

Authors:  Jing Gong; Huan Chen; Xiao-Yu Liu; Zhi-Xiu Wang; Wei Nie; Yong Qin
Journal:  Nat Commun       Date:  2016-07-08       Impact factor: 14.919
  9 in total

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