Literature DB >> 20863105

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

Jun Hee Lee1, Yandong Zhang, Samuel J Danishefsky.   

Abstract

A sequence consisting of a Lewis acid-catalyzed Diels-Alder reaction on a 2-halocyclohexenone, followed by reductive alkylation, provides a route to trans-fused octalinones bearing angular methyl groups with functionality corresponding to that which would have been possible from a trans-directed Diels-Alder reaction.

Entities:  

Mesh：

Substances：

Year:  2010        PMID： 20863105      PMCID： PMC2974171          DOI： 10.1021/ja1073855

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


  8 in total

1.  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

2.  Computer-assisted design of complex organic syntheses.

Authors:  E J Corey; W T Wipke
Journal:  Science       Date:  1969-10-10       Impact factor: 47.728

Review 3.  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

4.  Stereoselective construction of halogenated quaternary stereogenic centers via catalytic asymmetric Diels-Alder reaction.

Authors:  Kazutaka Shibatomi; Kentaro Futatsugi; Fumito Kobayashi; Seiji Iwasa; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2010-04-28       Impact factor: 15.419

5.  Diels-Alder routes to angularly halogenated cis-fused bicyclic ketones: Readily accessible cyclynone intermediates.

Authors:  Jun Hee Lee; Samuel J Danishefsky
Journal:  Tetrahedron Lett       Date:  2010-09-01       Impact factor: 2.415

6.  Syntheses of Isomerically Pure Reference Octalins and Hydrindanes.

Authors:  Jun Hee Lee; Woo Han Kim; Samuel J Danishefsky
Journal:  Tetrahedron Lett       Date:  2009-09-30       Impact factor: 2.415

7.  A Diels-Alder Route to Angularly Functionalized Bicyclic Structures.

Authors:  Woo Han Kim; Jun Hee Lee; Baptiste Aussedat; Samuel J Danishefsky
Journal:  Tetrahedron       Date:  2010-08-01       Impact factor: 2.457

8.  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
  8 in total
  10 in total

1.  Antarafacial mediation of oxygen delivery by a phenylsulfinyl group in the epoxidation of proximal double bonds: intramolecular trapping of an early Pummerer intermediate with stereoelectronic control.

Authors:  Yandong Zhang; Jun Hee Lee; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2010-12-23       Impact factor: 15.419

2.  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

3.  Synthesis of Angularly Substituted trans-Fused Decalins through a Metallacycle-Mediated Annulative Cross-Coupling Cascade.

Authors:  Haruki Mizoguchi; Glenn C Micalizio
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-10       Impact factor: 15.336

4.  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

5.  Enhancing the scope of the Diels-Alder reaction through isonitrile chemistry: emergence of a new class of acyl-activated dienophiles.

Authors:  Steven D Townsend; Xiangyang Wu; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2012-06-18       Impact factor: 15.419

6.  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

7.  Radical Cation Cycloadditions Using Cleavable Redox Auxiliaries.

Authors:  Shishi Lin; Shane D Lies; Christopher S Gravatt; Tehshik P Yoon
Journal:  Org Lett       Date:  2016-12-29       Impact factor: 6.005

8.  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

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

Authors:  Audrey G Ross; Xiaohua Li; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2012-09-18       Impact factor: 15.419

10.  Rhodium(i)-catalyzed asymmetric [4 + 2] cycloaddition reactions of 2-alkylenecyclobutanols with cyclic enones through C-C bond cleavage: efficient access to trans-bicyclic compounds.

Authors:  Xinxin Zheng; Rui Guo; Guozhu Zhang; Dayong Zhang
Journal:  Chem Sci       Date:  2018-01-08       Impact factor: 9.825
  10 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.