Literature DB >> 25045072

Synthesis of (±)-tetrapetalone A-Me aglycon.

Peter N Carlsen1, Tyler J Mann, Amir H Hoveyda, Alison J Frontier.   

Abstract

The first synthesis of (±)-tetrapetalone A-Me aglycon is described. Key bond-forming reactions include Nazarov cyclization, a ring-closing metathesis promoted with complete diastereoselectivity by a chiral molybdenum-based complex, tandem conjugate reduction/intramolecular aldol cyclization, and oxidative dearomatization.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  cross-coupling; cyclization; metathesis; natural products; polycycles

Mesh：

Substances：

Year:  2014        PMID： 25045072      PMCID： PMC4260470          DOI： 10.1002/anie.201404410

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  45 in total

1.  Highly satisfactory procedures for the Pd-catalyzed cross coupling of aryl electrophiles with in situ generated alkynylzinc derivatives.

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2.  Cyclohexadienone ketals and quinols: four building blocks potentially useful for enantioselective synthesis.

Authors:  D Magdziak; S J Meek; T R R Pettus
Journal:  Chem Rev       Date:  2004-03       Impact factor: 60.622

Review 3.  The remarkable metal-catalysed olefin metathesis reaction.

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4.  Metathesis in total synthesis.

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Journal:  Chem Commun (Camb)       Date:  2011-04-26       Impact factor: 6.222

5.  Structure conservation in lipoxygenases: structural analysis of soybean lipoxygenase-1 and modeling of human lipoxygenases.

Authors:  S T Prigge; J C Boyington; B J Gaffney; L M Amzel
Journal:  Proteins       Date:  1996-03

6.  Evolution of a fourth generation catalyst for the amination and thioetherification of aryl halides.

Authors:  John F Hartwig
Journal:  Acc Chem Res       Date:  2008-11-18       Impact factor: 22.384

7.  Following an ISES lead: the first examples of asymmetric Ni(0)-mediated allylic amination.

Authors:  David B Berkowitz; Gourhari Maiti
Journal:  Org Lett       Date:  2004-08-05       Impact factor: 6.005

8.  Synthetic study on tetrapetalones: stereoselective cyclization of N-acyliminium ion to construct substituted 1-benzazepines.

Authors:  Cheng Li; Xinyu Li; Ran Hong
Journal:  Org Lett       Date:  2009-09-17       Impact factor: 6.005

9.  Diels-Alder construction of regiodifferentiated meta-amino phenols and derivatives.

Authors:  Marisa G Weaver; Wen-Ju Bai; Stephen K Jackson; Thomas R R Pettus
Journal:  Org Lett       Date:  2014-02-13       Impact factor: 6.005

10.  Evolution of catalytic stereoselective olefin metathesis: from ancillary transformation to purveyor of stereochemical identity.

Authors:  Amir H Hoveyda
Journal:  J Org Chem       Date:  2014-04-10       Impact factor: 4.354
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  6 in total

1.  Synthesis of Chiral Tetramic Acids: Preparation of (S)-5-Benzylpyrrolidine-2,4-dione from L-Phenylalanine Methyl Ester Hydrochloride.

Authors:  Kyle M Lambert; Austin W Medley; Amy C Jackson; Lauren E Markham; John L Wood
Journal:  Organic Synth       Date:  2019

2.  Studies toward the AB ring system of the tetrapetalone natural products.

Authors:  Peter Carlsen; Chao Jiang; Ildiko R Herrick; Alison J Frontier
Journal:  Tetrahedron       Date:  2015-09-02       Impact factor: 2.457

Review 3.  Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions.

Authors:  Paula Ruiz-Castillo; Stephen L Buchwald
Journal:  Chem Rev       Date:  2016-09-30       Impact factor: 60.622

4.  Palladium-Catalyzed Decarbonylative Dehydration for the Synthesis of α-Vinyl Carbonyl Compounds and Total Synthesis of (-)-Aspewentins A, B, and C.

Authors:  Yiyang Liu; Scott C Virgil; Robert H Grubbs; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2015-07-29       Impact factor: 15.336

5.  A general diastereoselective catalytic vinylogous aldol reaction among tetramic acid-derived pyrroles.

Authors:  Jonathan G David; Wen-Ju Bai; Marisa G Weaver; Thomas R R Pettus
Journal:  Org Lett       Date:  2014-08-13       Impact factor: 6.005

6.  Synthesis of a Ribose-Incorporating Medium Ring Scaffold via a Challenging Ring-Closing Metathesis Reaction.

Authors:  Stuart S Rankin; John J Caldwell; Nora B Cronin; Rob L M van Montfort; Ian Collins
Journal:  European J Org Chem       Date:  2016-08-15
  6 in total

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