Literature DB >> 27818534

An enantioselective synthesis of the C3-C21 segment of the macrolide immunosuppressive agent FR252921.

Arun K Ghosh1, Samuel Rodriguez1.   

Abstract

An enantioselective synthesis of the C3-C21 segment of the novel immunosuppressant FR252921 is described. The C12 and C13 stereogenic centers were constructed by a non-aldol process utilizing optically active 4-phenylbutyrolactone. The C18 stereogenic center was installed using Braun's highly diastereoselective acetate aldol reaction. Other key steps involved Curtius rearrangement and Horner-Wadsworth-Emmons olefination reactions.

Entities:  

Keywords:  FR252921; Macrolide; Synthesis; aldol reaction; asymmetric; asymmetric reduction; immunosuppressive

Year:  2016        PMID： 27818534      PMCID： PMC5094281          DOI： 10.1016/j.tetlet.2016.05.067

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  17 in total

1.  FR252921, a novel immunosuppressive agent isolated from Pseudomonas fluorescens no. 408813. I. Taxonomy, fermentation, isolation, physico-chemical properties and biological activities of FR252921, FR252922 and FR256523.

Authors:  Kiyotaka Fujine; Miho Tanaka; Keisuke Ohsumi; Michizane Hashimoto; Shigehiro Takase; Hirotsugu Ueda; Motohiro Hino; Takashi Fujii
Journal:  J Antibiot (Tokyo)       Date:  2003-02       Impact factor: 2.649

2.  FR252921, a novel immunosuppressive agent isolated from Pseudomonas fluorescens no. 408813 II. In vitro property and mode of action.

Authors:  Kiyotaka Fujine; Fumie Abe; Nobuo Seki; Hirotsugu Ueda; Motohiro Hino; Takashi Fujii
Journal:  J Antibiot (Tokyo)       Date:  2003-02       Impact factor: 2.649

3.  FR252921, a novel immunosuppressive agent isolated from Pseudomonas fluorescens no. 408813 III. In vivo activities.

Authors:  Kiyotaka Fujine; Hirotsugu Ueda; Motohiro Hino; Takashi Fujii
Journal:  J Antibiot (Tokyo)       Date:  2003-02       Impact factor: 2.649

4.  A mild and selective method for the hydrolysis of esters with trimethyltin hydroxide.

Authors:  K C Nicolaou; Anthony A Estrada; Mark Zak; Sang Hyup Lee; Brian S Safina
Journal:  Angew Chem Int Ed Engl       Date:  2005-02-18       Impact factor: 15.336

5.  Synthesis and stereochemical assignment of FR252921, a promising immunosuppressant.

Authors:  J Russell Falck; Anyu He; Hiroki Fukui; Hideyuki Tsutsui; Akella Radha
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

Review 6.  The mechanism of action of cyclosporin A and FK506.

Authors:  S Ho; N Clipstone; L Timmermann; J Northrop; I Graef; D Fiorentino; J Nourse; G R Crabtree
Journal:  Clin Immunol Immunopathol       Date:  1996-09

7.  Differential effects of cyclosporin A and tacrolimus on magnesium influx in Caco2 cells.

Authors:  Elodie Gouadon; Florence Lecerf; Michèle German-Fattal
Journal:  J Pharm Pharm Sci       Date:  2012       Impact factor: 2.327

8.  Stereoselective synthesis of pseudopeptide microbial agent AI-77-B.

Authors:  A K Ghosh; A Bischoff; J Cappiello
Journal:  Org Lett       Date:  2001-08-23       Impact factor: 6.005

9.  Synthesis of two bioactive natural products: FR252921 and pseudotrienic acid B.

Authors:  Dominique Amans; Véronique Bellosta; Janine Cossy
Journal:  Chemistry       Date:  2009       Impact factor: 5.236

10.  Asymmetric synthesis of anti-aldol segments via a nonaldol route: synthetic applications to statines and (-)-tetrahydrolipstatin.

Authors:  Arun K Ghosh; Khriesto Shurrush; Sarang Kulkarni
Journal:  J Org Chem       Date:  2009-06-19       Impact factor: 4.354
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  1 in total

1.  A Domino 10-Step Total Synthesis of FR252921 and Its Analogues, Complex Macrocyclic Immunosuppressants.

Authors:  Yong Chen; Guilhem Coussanes; Caroline Souris; Paul Aillard; Dainis Kaldre; Kathrin Runggatscher; Stefan Kubicek; Giovanni Di Mauro; Boris Maryasin; Nuno Maulide
Journal:  J Am Chem Soc       Date:  2019-08-22       Impact factor: 16.383
  1 in total

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