Literature DB >> 26236051

Total Synthesis of Clavosolide A via Tandem Allylic Oxidation/Oxa-Conjugate Addition Reaction.

Joseph B Baker1, Hyoungsu Kim2, Jiyong Hong1.   

Abstract

The tandem allylic oxidation/oxa-conjugate addition reaction promoted by the gem-disubstituent effect in conjunction with the NHC-mediated oxidative esterification was explored for the facile synthesis of clavosolide A.

Entities:  

Keywords:  clavosolide; gem-disubstituent effect; natural product; oxa-conjugate addition; tandem reaction; tetrahydropyran; total synthesis

Year:  2015        PMID： 26236051      PMCID： PMC4518467          DOI： 10.1016/j.tetlet.2014.11.135

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  17 in total

1.  N-Heterocyclic carbene catalyzed oxidative macrolactonization: total synthesis of (+)-dactylolide.

Authors:  Kiyoun Lee; Hyoungsu Kim; Jiyong Hong
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-26       Impact factor: 15.336

2.  Total synthesis, structural revision, and absolute configuration of (-)-clavosolide [corrected] A.

Authors:  Jung Beom Son; Si Nae Kim; Na Yeong Kim; Duck Hyung Lee
Journal:  Org Lett       Date:  2006-02-16       Impact factor: 6.005

3.  A formal synthesis of SCH 351448.

Authors:  Heekwang Park; Hyoungsu Kim; Jiyong Hong
Journal:  Org Lett       Date:  2011-06-21       Impact factor: 6.005

4.  A stereoselective formal synthesis of leucascandrolide A.

Authors:  Kiyoun Lee; Hyoungsu Kim; Jiyong Hong
Journal:  Org Lett       Date:  2011-04-29       Impact factor: 6.005

5.  Clavosolides A and B, dimeric macrolides from the Philippines sponge Myriastra clavosa.

Authors:  M Rama Rao; D John Faulkner
Journal:  J Nat Prod       Date:  2002-03       Impact factor: 4.050

6.  Total synthesis of the marine natural product (-)-clavosolide A.

Authors:  Conor S Barry; Jon D Elsworth; Peter T Seden; Nick Bushby; John R Harding; Roger W Alder; Christine L Willis
Journal:  Org Lett       Date:  2006-07-20       Impact factor: 6.005

7.  Cyclopropane compatibility with oxidative carbocation formation: total synthesis of clavosolide A.

Authors:  GuangRong Peh; Paul E Floreancig
Journal:  Org Lett       Date:  2012-10-24       Impact factor: 6.005

8.  Stereoselective synthesis of 2,6-cis-tetrahydropyrans through a tandem allylic oxidation/oxa-Michael reaction promoted by the gem-disubstituent effect: synthesis of (+)-neopeltolide macrolactone.

Authors:  Hyoungsu Kim; Yongho Park; Jiyong Hong
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

9.  Synthesis of lactones using substituted benzoic anhydride as a coupling reagent.

Authors:  Isamu Shiina; Hiroki Fukui; Akane Sasaki
Journal:  Nat Protoc       Date:  2007       Impact factor: 13.491

10.  N-heterocyclic carbene-catalyzed oxidation of unactivated aldehydes to esters.

Authors:  Brooks E Maki; Karl A Scheidt
Journal:  Org Lett       Date:  2008-08-30       Impact factor: 6.005
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  3 in total

1.  Total Synthesis of Clavosolide A via Asymmetric Alcohol-Mediated Carbonyl Allylation: Beyond Protecting Groups or Chiral Auxiliaries in Polyketide Construction.

Authors:  James M Cabrera; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2019-06-24       Impact factor: 15.336

2.  Enantioselective Alcohol C-H Functionalization for Polyketide Construction: Unlocking Redox-Economy and Site-Selectivity for Ideal Chemical Synthesis.

Authors:  Jiajie Feng; Zachary A Kasun; Michael J Krische
Journal:  J Am Chem Soc       Date:  2016-04-26       Impact factor: 15.419

3.  Tandem Allylboration-Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (-)-Clavosolide A.

Authors:  Alba Millán; James R Smith; Jack L-Y Chen; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2016-01-14       Impact factor: 15.336
  3 in total

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