Literature DB >> 23095114

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

GuangRong Peh1, Paul E Floreancig.   

Abstract

Cyclopropane-substituted allylic ethers react with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone to form oxocarbenium ions with no competitive ring cleavage. This reaction can be used for the preparation of cyclopropane-substituted tetrahydropyrans. The protocol was used as a key step in the total synthesis of the sponge-derived macrolide clavosolide A.

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Year:  2012        PMID： 23095114      PMCID： PMC3532433          DOI： 10.1021/ol302744t

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


  23 in total

1.  Enantioselective synthesis of cyclopropanes by aldehyde homologation.

Authors:  Christina A Risatti; Richard E Taylor
Journal:  Angew Chem Int Ed Engl       Date:  2004-12-10       Impact factor: 15.336

2.  Total synthesis of theopederin D.

Authors:  Michael E Green; Jason C Rech; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  Synthesis of sulfur-containing heterocycles through oxidative carbon-hydrogen bond functionalization.

Authors:  Yubo Cui; Paul E Floreancig
Journal:  Org Lett       Date:  2012-03-15       Impact factor: 6.005

4.  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

5.  Regiocontrolled Ru-catalyzed addition of carboxylic acids to alkynes: practical protocols for the synthesis of vinyl esters.

Authors:  Lukas J Goossen; Jens Paetzold; Debasis Koley
Journal:  Chem Commun (Camb)       Date:  2003-03-21       Impact factor: 6.222

6.  Alkyne hydrosilylation catalyzed by a cationic ruthenium complex: efficient and general trans addition.

Authors:  Barry M Trost; Zachary T Ball
Journal:  J Am Chem Soc       Date:  2005-12-21       Impact factor: 15.419

7.  Copper-catalyzed enantioselective synthesis of trans-1-alkyl-2-substituted cyclopropanes via tandem conjugate addition-intramolecular enolate trapping.

Authors:  Tim den Hartog; Alena Rudolph; Beatriz Maciá; Adriaan J Minnaard; Ben L Feringa
Journal:  J Am Chem Soc       Date:  2010-10-20       Impact factor: 15.419

8.  Total synthesis of the marine metabolite (-)-clavosolide D.

Authors:  Peter T Seden; Jonathan P H Charmant; Christine L Willis
Journal:  Org Lett       Date:  2008-03-21       Impact factor: 6.005

9.  Oxidative carbocation formation in macrocycles: synthesis of the neopeltolide macrocycle.

Authors:  Wangyang Tu; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

10.  An experimental and computational approach to defining structure/reactivity relationships for intramolecular addition reactions to bicyclic epoxonium ions.

Authors:  Shuangyi Wan; Hakan Gunaydin; K N Houk; Paul E Floreancig
Journal:  J Am Chem Soc       Date:  2007-06-05       Impact factor: 15.419
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  10 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.  Total synthesis of cyanolide A in the absence of protecting groups, chiral auxiliaries, or premetalated carbon nucleophiles.

Authors:  Andrew R Waldeck; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2013-03-11       Impact factor: 15.336

Review 3.  Polyketide construction via hydrohydroxyalkylation and related alcohol C-H functionalizations: reinventing the chemistry of carbonyl addition.

Authors:  Anne-Marie R Dechert-Schmitt; Daniel C Schmitt; Xin Gao; Takahiko Itoh; Michael J Krische
Journal:  Nat Prod Rep       Date:  2014-02-11       Impact factor: 13.423

4.  Bimolecular Coupling Reactions through Oxidatively Generated Aromatic Cations: Scope and Stereocontrol.

Authors:  Yubo Cui; Louis A Villafane; Dane J Clausen; Paul E Floreancig
Journal:  Tetrahedron       Date:  2013-09-09       Impact factor: 2.457

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

Authors:  Joseph B Baker; Hyoungsu Kim; Jiyong Hong
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

6.  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

7.  Spiroacetal formation through telescoped cycloaddition and carbon-hydrogen bond functionalization: total synthesis of bistramide A.

Authors:  Xun Han; Paul E Floreancig
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-04       Impact factor: 15.336

Review 8.  Quinone-Catalyzed Selective Oxidation of Organic Molecules.

Authors:  Alison E Wendlandt; Shannon S Stahl
Journal:  Angew Chem Int Ed Engl       Date:  2015-11-04       Impact factor: 15.336

Review 9.  Contemporary Strategies for the Synthesis of Tetrahydropyran Derivatives: Application to Total Synthesis of Neopeltolide, a Marine Macrolide Natural Product.

Authors:  Haruhiko Fuwa
Journal:  Mar Drugs       Date:  2016-03-25       Impact factor: 5.118

10.  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
  10 in total

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