Literature DB >> 22950514

Intramolecular Diels-Alder reactions of cycloalkenones: translation of high endo selectivity to trans junctions.

Audrey G Ross1, Xiaohua Li, Samuel J Danishefsky.   

Abstract

Intramolecular Diels-Alder reactions of cyclobutenone and larger cycloalkenones are described. High levels of endo addition attained from Lewis acid catalysis translate to trans hydrindene junctions upon fragmentation of the tricyclic adducts.

Entities:  

Mesh：

Substances：

Year:  2012        PMID： 22950514      PMCID： PMC3464979          DOI： 10.1021/ja307708q

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


  14 in total

1.  A Short Total Synthesis of Kuehneromycin A This work was generously supported by the Deutsche Forschungsgemeinschaft and the Fazit-Stiftung. We are grateful to Prof. W. Steglich, Ludwig-Maximilians-Universität München, for copies of spectra of natural kuehneromycin A and for recording 600 MHz (1)H NMR spectra of our synthetic sample. We thank BASF AG, Ludwigshafen, Germany, Pfizer AG, Karlsruhe, Germany, Haarmann & Reimer GmbH, Holzminden, Germany, Wacker GmbH, Burghausen, Germany, DEGUSSA AG, Frankfurt a. M., Germany and Bayer AG, Leverkusen, Germany, for chemicals and laboratory equipment.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-08-04       Impact factor: 15.336

Review 2.  Recent advances in natural product synthesis by using intramolecular Diels-Alder reactions.

Authors:  Ken-Ichi Takao; Ryosuke Munakata; Kin-ichi Tadano
Journal:  Chem Rev       Date:  2005-12       Impact factor: 60.622

3.  Pattern recognition in retrosynthetic analysis: snapshots in total synthesis.

Authors:  Rebecca M Wilson; Samuel J Danishefsky
Journal:  J Org Chem       Date:  2007-06-08       Impact factor: 4.354

Review 4.  The Diels--Alder reaction in total synthesis.

Authors:  K C Nicolaou; Scott A Snyder; Tamsyn Montagnon; Georgios Vassilikogiannakis
Journal:  Angew Chem Int Ed Engl       Date:  2002-05-17       Impact factor: 15.336

Review 5.  Catalytic enantioselective Diels--Alder reactions: methods, mechanistic fundamentals, pathways, and applications.

Authors:  E J Corey
Journal:  Angew Chem Int Ed Engl       Date:  2002-05-17       Impact factor: 15.336

6.  A straightforward route to functionalized trans-Diels-Alder motifs.

Authors:  Jun Hee Lee; Yandong Zhang; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2010-10-20       Impact factor: 15.419

7.  Further Expansion of the trans-Diels-Alder Paradigm: Reductive Alkylation of α-Cyanoketones.

Authors:  Feng Peng; Robin E Grote; Samuel J Danishefsky
Journal:  Tetrahedron Lett       Date:  2011-08-03       Impact factor: 2.415

8.  Origins of stereoselectivity in the trans Diels-Alder paradigm.

Authors:  Robert S Paton; Joel L Mackey; Woo Han Kim; Jun Hee Lee; Samuel J Danishefsky; K N Houk
Journal:  J Am Chem Soc       Date:  2010-07-14       Impact factor: 15.419

9.  Cyclobutenone as a highly reactive dienophile: expanding upon Diels-Alder paradigms.

Authors:  Xiaohua Li; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2010-08-18       Impact factor: 15.419

10.  Improved dienophilicity of nitrocycloalkenes: prospects for the development of a trans-Diels-Alder paradigm.

Authors:  Woo Han Kim; Jun Hee Lee; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2009-09-09       Impact factor: 15.419
View more
  10 in total

1.  Pattern recognition analysis in complex molecule synthesis and the preparation of iso-Diels-Alder motifs.

Authors:  Feng Peng; Robin E Grote; Rebecca M Wilson; Samuel J Danishefsky
Journal:  Proc Natl Acad Sci U S A       Date:  2013-06-19       Impact factor: 11.205

2.  Synthesis and Applications of Hajos-Parrish Ketone Isomers.

Authors:  James M Eagan; Masahiro Hori; Jianbin Wu; Kyalo Stephen Kanyiva; Scott A Snyder
Journal:  Angew Chem Int Ed Engl       Date:  2015-05-14       Impact factor: 15.336

3.  Stereospecific cis- and trans-ring fusions arising from common intermediates.

Authors:  Steven D Townsend; Audrey G Ross; Kai Liu; Samuel J Danishefsky
Journal:  Proc Natl Acad Sci U S A       Date:  2014-05-19       Impact factor: 11.205

4.  The Development of Alkoxide-Directed Metallacycle-Mediated Annulative Cross-Coupling Chemistry.

Authors:  Glenn C Micalizio; Haruki Mizoguchi
Journal:  Isr J Chem       Date:  2016-11-09       Impact factor: 3.333

5.  Palladium-catalyzed enantioselective Heck alkenylation of acyclic alkenols using a redox-relay strategy.

Authors:  Harshkumar H Patel; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2015-03-09       Impact factor: 15.419

6.  Halocycloalkenones as Diels-Alder dienophiles. Applications to generating useful structural patterns.

Authors:  Audrey G Ross; Steven D Townsend; Samuel J Danishefsky
Journal:  J Org Chem       Date:  2012-11-27       Impact factor: 4.354

7.  Intramolecular Diels-Alder reactions of cycloalkenones: stereoselectivity, Lewis acid acceleration, and halogen substituent effects.

Authors:  Hung V Pham; Robert S Paton; Audrey G Ross; Samuel J Danishefsky; K N Houk
Journal:  J Am Chem Soc       Date:  2014-02-04       Impact factor: 15.419

8.  Guiding a divergent reaction by photochemical control: bichromatic selective access to levulinates and butenolides.

Authors:  Revannath L Sutar; Saumik Sen; Or Eivgi; Gal Segalovich; Igor Schapiro; Ofer Reany; N Gabriel Lemcoff
Journal:  Chem Sci       Date:  2017-12-18       Impact factor: 9.825

9.  Stereocontrolled synthesis and functionalization of cyclobutanes and cyclobutanones.

Authors:  Francesco Secci; Angelo Frongia; Pier Paolo Piras
Journal:  Molecules       Date:  2013-12-13       Impact factor: 4.411

10.  Pd-Catalyzed Cascade Reactions of Aziridines: One-Step Access to Complex Tetracyclic Amines.

Authors:  Jonathan P Knowles; Hannah G Steeds; Maria Schwarz; Francesca Latter; Kevin I Booker-Milburn
Journal:  Org Lett       Date:  2021-06-16       Impact factor: 6.005
  10 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.