Literature DB >> 21780806

Total synthesis of bryostatin 7 via C-C bond-forming hydrogenation.

Yu Lu1, Sang Kook Woo, Michael J Krische.   

Abstract

The marine macrolide bryostatin 7 is prepared in 20 steps (longest linear sequence) and 36 total steps with five C-C bonds formed using hydrogenative methods. This approach represents the most concise synthesis of any bryostatin reported, to date.

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Year:  2011        PMID： 21780806      PMCID： PMC3164899          DOI： 10.1021/ja205673e

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


  51 in total

1.  Total synthesis of bryostatin 1.

Authors:  Gary E Keck; Yam B Poudel; Thomas J Cummins; Arnab Rudra; Jonathan A Covel
Journal:  J Am Chem Soc       Date:  2010-12-22       Impact factor: 15.419

2.  Synthetic studies toward the bryostatins: a substrate-controlled approach to the A-ring.

Authors:  Gary E Keck; Dennie S Welch; Paige K Vivian
Journal:  Org Lett       Date:  2006-08-17       Impact factor: 6.005

3.  Design, synthesis, and biological evaluation of a potent, PKC selective, B-ring analog of bryostatin.

Authors:  Paul A Wender; Vishal A Verma
Journal:  Org Lett       Date:  2006-04-27       Impact factor: 6.005

4.  Identification of the putative bryostatin polyketide synthase gene cluster from "Candidatus Endobugula sertula", the uncultivated microbial symbiont of the marine bryozoan Bugula neritina.

Authors:  Sebastian Sudek; Nicole B Lopanik; Laura E Waggoner; Mark Hildebrand; Christine Anderson; Haibin Liu; Amrish Patel; David H Sherman; Margo G Haygood
Journal:  J Nat Prod       Date:  2007-01       Impact factor: 4.050

5.  The design, synthesis, and evaluation of C7 diversified bryostatin analogs reveals a hot spot for PKC affinity.

Authors:  Paul A Wender; Vishal A Verma
Journal:  Org Lett       Date:  2008-06-28       Impact factor: 6.005

6.  Total synthesis of a 20-deoxybryostatin.

Authors:  Anthony P Green; Alan T L Lee; Eric J Thomas
Journal:  Chem Commun (Camb)       Date:  2011-05-26       Impact factor: 6.222

7.  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

8.  Therapeutic effects of PKC activators in Alzheimer's disease transgenic mice.

Authors:  René Etcheberrigaray; Mathew Tan; Ilse Dewachter; Cuno Kuipéri; Ingrid Van der Auwera; Stefaan Wera; Lixin Qiao; Barry Bank; Thomas J Nelson; Alan P Kozikowski; Fred Van Leuven; Daniel L Alkon
Journal:  Proc Natl Acad Sci U S A       Date:  2004-07-19       Impact factor: 11.205

9.  Concise synthesis of the bryostatin A-ring via consecutive C-C bond forming transfer hydrogenations.

Authors:  Yu Lu; Michael J Krische
Journal:  Org Lett       Date:  2009-07-16       Impact factor: 6.005

10.  Catalyst-directed diastereoselectivity in hydrogenative couplings of acetylene to alpha-chiral aldehydes: formal synthesis of all eight L-hexoses.

Authors:  Soo Bong Han; Jong Rock Kong; Michael J Krische
Journal:  Org Lett       Date:  2008-08-26       Impact factor: 6.005
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  41 in total

Review 1.  Neurotrophic natural products: chemistry and biology.

Authors:  Jing Xu; Michelle H Lacoske; Emmanuel A Theodorakis
Journal:  Angew Chem Int Ed Engl       Date:  2013-12-18       Impact factor: 15.336

2.  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

3.  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

Review 4.  Asymmetric Iridium-Catalyzed C-C Coupling of Chiral Diols via Site-Selective Redox-Triggered Carbonyl Addition.

Authors:  Inji Shin; Michael J Krische
Journal:  Top Curr Chem       Date:  2016

5.  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

6.  Inhibition of Chikungunya Virus-Induced Cell Death by Salicylate-Derived Bryostatin Analogues Provides Additional Evidence for a PKC-Independent Pathway.

Authors:  Daryl Staveness; Rana Abdelnabi; Katherine E Near; Yu Nakagawa; Johan Neyts; Leen Delang; Pieter Leyssen; Paul A Wender
Journal:  J Nat Prod       Date:  2016-02-22       Impact factor: 4.050

7.  Function Oriented Synthesis: Preparation and Initial Biological Evaluation of New A-Ring-Modified Bryologs.

Authors:  Paul A Wender; Jenny Reuber
Journal:  Tetrahedron       Date:  2011-12-23       Impact factor: 2.457

8.  Deletion of the C26 Methyl Substituent from the Bryostatin Analogue Merle 23 Has Negligible Impact on Its Biological Profile and Potency.

Authors:  Xiguang Zhao; Noemi Kedei; Alexandra Michalowski; Nancy E Lewin; Gary E Keck; Peter M Blumberg
Journal:  Chembiochem       Date:  2018-04-27       Impact factor: 3.164

9.  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 10.  Dynamics and Membrane Interactions of Protein Kinase C.

Authors:  Tatyana I Igumenova
Journal:  Biochemistry       Date:  2015-08-05       Impact factor: 3.162
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