Literature DB >> 22913543

Asymmetric catalytic synthesis of the proposed structure of trocheliophorolide B.

Barry M Trost1, Adrien Quintard.   

Abstract

A concise catalytic asymmetric synthesis of the proposed structure of trocheliophorolide B is reported. The synthetic sequence notably features an asymmetric acetaldehyde alkynylation, a Ru-catalyzed alder-ene reaction, and a Zn-ProPhenol ynone aldol condensation. Comparison with the reported data suggests a misassignment of the natural product structure.

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Year:  2012        PMID： 22913543      PMCID： PMC3439167          DOI： 10.1021/ol302074h

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


  13 in total

1.  Direct catalytic asymmetric aldol additions of methyl ynones. Spontaneous reversal in the sense of enantioinduction.

Authors:  Barry M Trost; Alec Fettes; Brock T Shireman
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2.  Dinuclear Zn-catalyzed asymmetric alkynylation of unsaturated aldehydes.

Authors:  Barry M Trost; Andrew H Weiss; Axel Jacobi von Wangelin
Journal:  J Am Chem Soc       Date:  2006-01-11       Impact factor: 15.419

Review 3.  Acetogenins from Annonaceae: recent progress in isolation, synthesis and mechanisms of action.

Authors:  Almudena Bermejo; Bruno Figadere; Maria-Carmen Zafra-Polo; Isabel Barrachina; Ernesto Estornell; Diego Cortes
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4.  Exploring biosynthetic relationships among furanocembranoids: synthesis of (-)-bipinnatin J, (+)-intricarene, (+)-rubifolide, and (+)-isoepilophodione B.

Authors:  Paul A Roethle; Paul T Hernandez; Dirk Trauner
Journal:  Org Lett       Date:  2006-12-07       Impact factor: 6.005

5.  Assignment of the structure of petrocortyne A by mixture syntheses of four candidate stereoisomers.

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Journal:  J Am Chem Soc       Date:  2005-12-07       Impact factor: 15.419

7.  Asymmetric catalytic alkynylation of acetaldehyde: application to the synthesis of (+)-tetrahydropyrenophorol.

Authors:  Barry M Trost; Adrien Quintard
Journal:  Angew Chem Int Ed Engl       Date:  2012-06-05       Impact factor: 15.336

8.  Direct catalytic asymmetric Mannich-type reactions of gamma-butenolides: effectiveness of Brønsted acid in chiral metal catalysis.

Authors:  Akitake Yamaguchi; Shigeki Matsunaga; Masakatsu Shibasaki
Journal:  Org Lett       Date:  2008-05-07       Impact factor: 6.005

9.  Total synthesis of (+)-azaspiracid-1. An exhibition of the intricacies of complex molecule synthesis.

Authors:  David A Evans; Lisbet Kvaernø; Travis B Dunn; André Beauchemin; Brian Raymer; Jason A Mulder; Edward J Olhava; Martin Juhl; Katsuji Kagechika; David A Favor
Journal:  J Am Chem Soc       Date:  2008-12-03       Impact factor: 15.419

10.  Recent progress on the total synthesis of acetogenins from Annonaceae.

Authors:  Nianguang Li; Zhihao Shi; Yuping Tang; Jianwei Chen; Xiang Li
Journal:  Beilstein J Org Chem       Date:  2008-12-05       Impact factor: 2.883
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  10 in total

1.  Metallacycle-Mediated Cross-Coupling in Natural Product Synthesis.

Authors:  Natasha F O'Rourke; Matthew J Kier; Glenn C Micalizio
Journal:  Tetrahedron       Date:  2016-09-07       Impact factor: 2.457

2.  Enantioselective syntheses of FR901464 and spliceostatin A: potent inhibitors of spliceosome.

Authors:  Arun K Ghosh; Zhi-Hua Chen
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3.  Catalytic Z-selective cross-metathesis with secondary silyl- and benzyl-protected allylic ethers: mechanistic aspects and applications to natural product synthesis.

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4.  Total synthesis of (-)-18-epi-peloruside A: an alkyne linchpin strategy.

Authors:  Barry M Trost; David J Michaelis; Sushant Malhotra
Journal:  Org Lett       Date:  2013-10-04       Impact factor: 6.005

Review 5.  Spliceostatins and Derivatives: Chemical Syntheses and Biological Properties of Potent Splicing Inhibitors.

Authors:  Arun K Ghosh; Jennifer L Mishevich; Melissa S Jurica
Journal:  J Nat Prod       Date:  2021-05-11       Impact factor: 4.803

6.  ProPhenol-catalyzed asymmetric additions by spontaneously assembled dinuclear main group metal complexes.

Authors:  Barry M Trost; Mark J Bartlett
Journal:  Acc Chem Res       Date:  2015-02-04       Impact factor: 22.384

7.  A highly efficient nano-sized Cu2O/SiO2 egg-shell catalyst for C-C coupling reactions.

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Journal:  RSC Adv       Date:  2018-02-07       Impact factor: 3.361

8.  Enantioselective total syntheses of FR901464 and spliceostatin A and evaluation of splicing activity of key derivatives.

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9.  Chagosensine: A Riddle Wrapped in a Mystery Inside an Enigma.

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Journal:  J Am Chem Soc       Date:  2020-03-20       Impact factor: 15.419

10.  Stereoselective total synthesis and structural revision of the diacetylenic diol natural products strongylodiols H and I.

Authors:  Pamarthi Gangadhar; Sayini Ramakrishna; Ponneri Venkateswarlu; Pabbaraja Srihari
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  10 in total

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