Literature DB >> 31061542

Short Enantioselective Formal Synthesis of (-)-Platencin.

Christian Defieber1, Justin T Mohr1,2, Gennadii A Grabovyi2, Brian M Stoltz1.   

Abstract

A short enantioselective formal synthesis of the antibiotic natural product platencin is reported. Key steps in the synthesis include enantioselective decarboxylation alkylation, aldehyde/olefin radical cyclization, and regioselective aldol cyclization.

Entities:  

Keywords:  Formal synthesis; alkylation; enantioconvergent; enantioselective; palladium

Year:  2018        PMID: 31061542      PMCID: PMC6498846          DOI: 10.1055/s-0037-1610437

Source DB:  PubMed          Journal:  Synthesis (Stuttg)        ISSN: 0039-7881            Impact factor:   3.157


  65 in total

1.  The enantioselective Tsuji allylation.

Authors:  Douglas C Behenna; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2004-11-24       Impact factor: 15.419

2.  Mechanistic aspects of thiyl radical-promoted acyl radical cyclization of formylenoate-cyclization versus oxidation.

Authors:  Kazuya Yoshikai; Tomoharu Hayama; Katsumi Nishimura; Ken-ichi Yamada; Kiyoshi Tomioka
Journal:  Chem Pharm Bull (Tokyo)       Date:  2005-05       Impact factor: 1.645

3.  Deracemization of quaternary stereocenters by Pd-catalyzed enantioconvergent decarboxylative allylation of racemic beta-ketoesters.

Authors:  Justin T Mohr; Douglas C Behenna; Andrew M Harned; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2005-10-28       Impact factor: 15.336

4.  An efficient synthesis of achiral and chiral 1,2,4-triazolium salts: bench stable precursors for N-heterocyclic carbenes.

Authors:  Mark S Kerr; Javier Read de Alaniz; Tomislav Rovis
Journal:  J Org Chem       Date:  2005-07-08       Impact factor: 4.354

5.  The catalytic enantioselective, protecting group-free total synthesis of (+)-dichroanone.

Authors:  Ryan M McFadden; Brian M Stoltz
Journal:  J Am Chem Soc       Date:  2006-06-21       Impact factor: 15.419

6.  Thiol-catalyzed acyl radical cyclization of alkenals.

Authors:  Kazuya Yoshikai; Tomoharu Hayama; Katsumi Nishimura; Ken-Ichi Yamada; Kiyoshi Tomioka
Journal:  J Org Chem       Date:  2005-01-21       Impact factor: 4.354

7.  Intramolecular conjugate addition of alkenyl and aryl functions to enones initiated by lithium-iodine exchange.

Authors:  E Piers; C L Harrison; C Zetina-Rocha
Journal:  Org Lett       Date:  2001-10-18       Impact factor: 6.005

Review 8.  Phosphinooxazolines--a new class of versatile, modular P,N-ligands for asymmetric catalysis.

Authors:  G Helmchen; A Pfaltz
Journal:  Acc Chem Res       Date:  2000-06       Impact factor: 22.384

9.  Synthesis and biochemical evaluation of phosphonoformate oligodeoxyribonucleotides.

Authors:  Christina M Yamada; Douglas J Dellinger; Marvin H Caruthers
Journal:  J Am Chem Soc       Date:  2006-04-19       Impact factor: 15.419

10.  Platensimycin is a selective FabF inhibitor with potent antibiotic properties.

Authors:  Jun Wang; Stephen M Soisson; Katherine Young; Wesley Shoop; Srinivas Kodali; Andrew Galgoci; Ronald Painter; Gopalakrishnan Parthasarathy; Yui S Tang; Richard Cummings; Sookhee Ha; Karen Dorso; Mary Motyl; Hiranthi Jayasuriya; John Ondeyka; Kithsiri Herath; Chaowei Zhang; Lorraine Hernandez; John Allocco; Angela Basilio; José R Tormo; Olga Genilloud; Francisca Vicente; Fernando Pelaez; Lawrence Colwell; Sang Ho Lee; Bruce Michael; Thomas Felcetto; Charles Gill; Lynn L Silver; Jeffery D Hermes; Ken Bartizal; John Barrett; Dennis Schmatz; Joseph W Becker; Doris Cully; Sheo B Singh
Journal:  Nature       Date:  2006-05-18       Impact factor: 49.962

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  2 in total

1.  Probing Trends in Enantioinduction via Substrate Design: Palladium-Catalyzed Decarboxylative Allylic Alkylation of α-Enaminones.

Authors:  Douglas C Duquette; Alexander Q Cusumano; Louise Lefoulon; Jared T Moore; Brian M Stoltz
Journal:  Org Lett       Date:  2020-06-16       Impact factor: 6.005

Review 2.  The Allylic Alkylation of Ketone Enolates.

Authors:  Lukas Junk; Uli Kazmaier
Journal:  ChemistryOpen       Date:  2020-09-10       Impact factor: 2.630

  2 in total

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