Literature DB >> 21639102

Total synthesis of the cyanolide A aglycon.

Michael R Gesinski1, Scott D Rychnovsky.   

Abstract

The synthesis of the potent molluscicide cyanolide A has been achieved in 10 steps without the use of protecting groups. The synthesis features a key Sakurai macrocyclization/dimerization reaction that simultaneously forms both tetrahydropyran rings and the macrocycle of the natural product.

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Year:  2011        PMID： 21639102      PMCID： PMC3133735          DOI： 10.1021/ja204228q

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


  32 in total

Review 1.  Schistosomiasis.

Authors:  Allen G P Ross; Paul B Bartley; Adrian C Sleigh; G Richard Olds; Yuesheng Li; Gail M Williams; Donald P McManus
Journal:  N Engl J Med       Date:  2002-04-18       Impact factor: 91.245

2.  Efficient synthetic access to a new family of highly potent bryostatin analogues via a Prins-driven macrocyclization strategy.

Authors:  Paul A Wender; Brian A Dechristopher; Adam J Schrier
Journal:  J Am Chem Soc       Date:  2008-05-02       Impact factor: 15.419

Review 3.  Human schistosomiasis.

Authors:  Bruno Gryseels; Katja Polman; Jan Clerinx; Luc Kestens
Journal:  Lancet       Date:  2006-09-23       Impact factor: 79.321

4.  Pyran annulation: asymmetric synthesis of 2,6-disubstituted-4-methylene tetrahydropyrans.

Authors:  Gary E Keck; Jonathan A Covel; Tobias Schiff; Tao Yu
Journal:  Org Lett       Date:  2002-04-04       Impact factor: 6.005

5.  A formal synthesis of psymberin.

Authors:  Ning Shangguan; Sezgin Kiren; Lawrence J Williams
Journal:  Org Lett       Date:  2007-02-24       Impact factor: 6.005

6.  Symmetric macrocycles by a Prins dimerization and macrocyclization strategy.

Authors:  Michael R Gesinski; Kwanruthai Tadpetch; Scott D Rychnovsky
Journal:  Org Lett       Date:  2009-11-19       Impact factor: 6.005

7.  Total synthesis of platensimycin and related natural products.

Authors:  K C Nicolaou; Ang Li; David J Edmonds; G Scott Tria; Shelby P Ellery
Journal:  J Am Chem Soc       Date:  2009-11-25       Impact factor: 15.419

Review 8.  Praziquantel.

Authors:  Donato Cioli; Livia Pica-Mattoccia
Journal:  Parasitol Res       Date:  2002-11-22       Impact factor: 2.289

9.  Enantioselective total synthesis of macrolide antitumor agent (-)-lasonolide A.

Authors:  Arun K Ghosh; Gangli Gong
Journal:  Org Lett       Date:  2007-03-17       Impact factor: 6.005

10.  Reduced susceptibility to praziquantel among naturally occurring Kenyan isolates of Schistosoma mansoni.

Authors:  Sandra D Melman; Michelle L Steinauer; Charles Cunningham; Laura S Kubatko; Ibrahim N Mwangi; Nirvana Barker Wynn; Martin W Mutuku; Diana M S Karanja; Daniel G Colley; Carla L Black; William Evan Secor; Gerald M Mkoji; Eric S Loker
Journal:  PLoS Negl Trop Dis       Date:  2009-08-18
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  15 in total

1.  Toward the Ideal Synthesis and Transformative Therapies: The Roles of Step Economy and Function Oriented Synthesis.

Authors:  Paul A Wender
Journal:  Tetrahedron       Date:  2013-06-07       Impact factor: 2.457

2.  Lead Diversification through a Prins-Driven Macrocyclization Strategy: Application to C13-Diversified Bryostatin Analogues.

Authors:  Paul A Wender; Kelvin L Billingsley
Journal:  Synthesis (Stuttg)       Date:  2013       Impact factor: 3.157

3.  Bi(OTf)3-, TfOH-, and TMSOTf-mediated, one-pot epoxide rearrangement, addition, and intramolecular silyl-modified Sakurai (ISMS) cascade toward dihydropyrans: comparison of catalysts and role of Bi(OTf)3.

Authors:  R Frederick Lambert; Robert J Hinkle; Stephen E Ammann; Yajing Lian; Jia Liu; Shane E Lewis; Robert D Pike
Journal:  J Org Chem       Date:  2011-10-25       Impact factor: 4.354

Review 4.  Feedstock Reagents in Metal-Catalyzed Carbonyl Reductive Coupling: Minimizing Preactivation for Efficiency in Target-Oriented Synthesis.

Authors:  Rosalie S Doerksen; Cole C Meyer; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-26       Impact factor: 15.336

5.  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

6.  A tandem isomerization/prins strategy: iridium(III)/Brønsted acid cooperative catalysis.

Authors:  Vince M Lombardo; Christopher D Thomas; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-11       Impact factor: 15.336

7.  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

8.  Total synthesis and structure-activity relationship study of the potent cAMP signaling agonist (-)-alotaketal A.

Authors:  Jinhua Huang; Jessica R Yang; Jin Zhang; Jiong Yang
Journal:  Org Biomol Chem       Date:  2013-04-12       Impact factor: 3.876

9.  Discovery, Total Synthesis and Key Structural Elements for the Immunosuppressive Activity of Cocosolide, a Symmetrical Glycosylated Macrolide Dimer from Marine Cyanobacteria.

Authors:  Sarath P Gunasekera; Yang Li; Ranjala Ratnayake; Danmeng Luo; Jeannette Lo; Joseph H Reibenspies; Zhengshuang Xu; Michael J Clare-Salzler; Tao Ye; Valerie J Paul; Hendrik Luesch
Journal:  Chemistry       Date:  2016-05-03       Impact factor: 5.236

Review 10.  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
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