Literature DB >> 16671773

Palladium asymmetric allylic alkylation of prochiral nucleophiles: horsfiline.

Barry M Trost1, Megan K Brennan.   

Abstract

[reaction; see text] The asymmetric synthesis of the oxindole alkaloid horsfiline is described. A palladium-catalyzed asymmetric allylic alkylation (AAA) is used to set the spiro(pyrrolidine-oxindole) stereogenic center.

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Year:  2006        PMID： 16671773      PMCID： PMC2565574          DOI： 10.1021/ol060298j

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


  7 in total

1.  Total Synthesis of (-)-Horsfiline via Asymmetric Nitroolefination.

Authors:  Gingipalli Lakshmaiah; Takeo Kawabata; Muhong Shang; Kaoru Fuji
Journal:  J Org Chem       Date:  1999-03-05       Impact factor: 4.354

2.  The Use of Salicylaldehyde Phenylhydrazone as an Indicator for the Titration of Organometallic Reagents.

Authors:  Brian E. Love; Edward G. Jones
Journal:  J Org Chem       Date:  1999-05-14       Impact factor: 4.354

3.  Palladium-catalyzed asymmetric allylation of prochiral nucleophiles: synthesis of 3-allyl-3-aryl oxindoles.

Authors:  Barry M Trost; Mathias U Frederiksen
Journal:  Angew Chem Int Ed Engl       Date:  2004-12-27       Impact factor: 15.336

4.  Novel phosphorus radical-based routes to horsfiline.

Authors:  John A Murphy; Régis Tripoli; Tanweer A Khan; Umesh W Mali
Journal:  Org Lett       Date:  2005-07-21       Impact factor: 6.005

5.  Azomethine ylide cycloaddition/reductive heterocyclization approach to oxindole alkaloids: asymmetric synthesis of (-)-horsfiline.

Authors:  G Cravotto; G B Giovenzana; T Pilati; M Sisti; G Palmisano
Journal:  J Org Chem       Date:  2001-12-14       Impact factor: 4.354

6.  A new route to spiropyrrolidinyl-oxindole alkaloids via iodide ion induced rearrangement of [(N-aziridinomethylthio)methylene]-2-oxindoles.

Authors:  U K Syam Kumar; H Ila; H Junjappa
Journal:  Org Lett       Date:  2001-12-27       Impact factor: 6.005

7.  Concise synthesis of (+/-)-horsfiline and (+/-)-coerulescine by tandem cyclisation of iodoaryl alkenyl azides.

Authors:  Dimitrios E Lizos; John A Murphy
Journal:  Org Biomol Chem       Date:  2003-01-07       Impact factor: 3.876
  7 in total
  13 in total

1.  The palladium catalyzed asymmetric addition of oxindoles and allenes: an atom-economical versatile method for the construction of chiral indole alkaloids.

Authors:  Barry M Trost; Jia Xie; Joshua D Sieber
Journal:  J Am Chem Soc       Date:  2011-11-30       Impact factor: 15.419

2.  Asymmetric synthesis of allenyl oxindoles and spirooxindoles by a catalytic enantioselective Saucy-Marbet Claisen rearrangement.

Authors:  Trung Cao; Joshua Deitch; Elizabeth C Linton; Marisa C Kozlowski
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-27       Impact factor: 15.336

3.  Rh(II)2-catalyzed synthesis of α-, β-, or δ-carbolines from aryl azides.

Authors:  Ashley L Pumphrey; Huijun Dong; Tom G Driver
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-26       Impact factor: 15.336

4.  Copper(II)- and palladium(II)-catalyzed enantioselective Claisen rearrangement of allyloxy- and propargyloxy-indoles to quaternary oxindoles and spirocyclic lactones.

Authors:  Trung Cao; Elizabeth C Linton; Joshua Deitch; Simon Berritt; Marisa C Kozlowski
Journal:  J Org Chem       Date:  2012-12-04       Impact factor: 4.354

5.  Direct Access to Highly Functionalized Heterocycles through the Condensation of Cyclic Imines and α-Oxoesters.

Authors:  Alexander Q Cusumano; Matthew W Boudreau; Joshua G Pierce
Journal:  J Org Chem       Date:  2017-12-05       Impact factor: 4.354

6.  Stereoselective Synthesis of Quaternary Pyrrolidine-2,3-diones and β-Amino Acids.

Authors:  Nataliia V Shymanska; Joshua G Pierce
Journal:  Org Lett       Date:  2017-05-24       Impact factor: 6.005

7.  A concise enantioselective synthesis of (-)-ranirestat.

Authors:  Barry M Trost; Maksim Osipov; Guangbin Dong
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

8.  A versatile synthesis of unsymmetrical 3,3'-bioxindoles: stereoselective Mukaiyama aldol reactions of 2-siloxyindoles with isatins.

Authors:  J Michael Ellis; Larry E Overman; Huw R Tanner; Jocelyn Wang
Journal:  J Org Chem       Date:  2008-10-15       Impact factor: 4.354

9.  Total synthesis of (±)-coerulescine and (±)-horsfiline.

Authors:  Mukund G Kulkarni; Attrimuni P Dhondge; Sanjay W Chavhan; Ajit S Borhade; Yunnus B Shaikh; Deekshaputra R Birhade; Mayur P Desai; Nagorao R Dhatrak
Journal:  Beilstein J Org Chem       Date:  2010-09-27       Impact factor: 2.883

10.  Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp(2) C-H and sp(3) C-H bonds.

Authors:  Nivesh Kumar; Santanu Ghosh; Subhajit Bhunia; Alakesh Bisai
Journal:  Beilstein J Org Chem       Date:  2016-06-08       Impact factor: 2.883
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