Literature DB >> 33488832

Progress in the total synthesis of inthomycins.

Bidyut Kumar Senapati1.   

Abstract

The inthomycin family of antibiotics, isolated from Streptomyces strains, are interesting molecules for synthesis due to their characteristic common oxazole polyene chiral allylic β-hydroxycarbonyl fragments and significant biological activities. The full structural motif of the inthomycins is found in several more complex natural products including the oxazolomycins, 16-methyloxazolomycin, curromycins A and B, and KSM-2690. This review summarises the application of various efforts towards the synthesis of inthomycins and their analogues systematically.
Copyright © 2021, Senapati; licensee Beilstein-Institut.

Entities:  

Keywords:  Stille coupling; antibiotics; inthomycins; oxazololomycin; total synthesis

Year:  2021        PMID: 33488832      PMCID: PMC7801802          DOI: 10.3762/bjoc.17.7

Source DB:  PubMed          Journal:  Beilstein J Org Chem        ISSN: 1860-5397            Impact factor:   2.883


  37 in total

1.  A Method for Iodination of Oxazoles at C-4 via 2-Lithiooxazoles.

Authors:  Edwin Vedejs; Leza M. Luchetta
Journal:  J Org Chem       Date:  1999-02-05       Impact factor: 4.354

2.  Significant enhancement of the Stille reaction with a new combination of reagents-copper(I) iodide with cesium fluoride.

Authors:  Simon P H Mee; Victor Lee; Jack E Baldwin
Journal:  Chemistry       Date:  2005-05-20       Impact factor: 5.236

Review 3.  Total synthesis of oxazolomycins.

Authors:  Jun Ishihara; Susumi Hatakeyama
Journal:  Chem Rec       Date:  2014-07-28       Impact factor: 6.771

4.  New antibiotics phthoxazolins B, C and D produced by Streptomyces sp. KO-7888.

Authors:  K Shiomi; N Arai; M Shinose; Y Takahashi; H Yoshida; J Iwabuchi; Y Tanaka; S Omura
Journal:  J Antibiot (Tokyo)       Date:  1995-07       Impact factor: 2.649

5.  Carreira alkynylations with paraformaldehyde. a mild and convenient protocol for the hydroxymethylation of complex base-sensitive terminal acetylenes via alkynylzinc triflates.

Authors:  Karl J Hale; Ziyue Xiong; Liping Wang; Soraya Manaviazar; Ryan Mackle
Journal:  Org Lett       Date:  2014-12-24       Impact factor: 6.005

Review 6.  The expanded horizon for microbial metabolites--a review.

Authors:  S Omura
Journal:  Gene       Date:  1992-06-15       Impact factor: 3.688

7.  Phthoxazolin A, a specific inhibitor of cellulose biosynthesis from microbial origin. I. Discovery, taxonomy of producing microorganism, fermentation, and biological activity.

Authors:  Y Tanaka; I Kanaya; Y Takahashi; M Shinose; H Tanaka; S Omura
Journal:  J Antibiot (Tokyo)       Date:  1993-08       Impact factor: 2.649

8.  Mosher ester analysis for the determination of absolute configuration of stereogenic (chiral) carbinol carbons.

Authors:  Thomas R Hoye; Christopher S Jeffrey; Feng Shao
Journal:  Nat Protoc       Date:  2007       Impact factor: 13.491

9.  Stereoselective synthesis of dienyl-carboxylate building blocks: formal synthesis of inthomycin C.

Authors:  Caroline Souris; Frédéric Frébault; Ashay Patel; Davide Audisio; K N Houk; Nuno Maulide
Journal:  Org Lett       Date:  2013-06-13       Impact factor: 6.005

10.  Catalytic asymmetric acyl halide-aldehyde cyclocondensation reactions of substituted ketenes.

Authors:  Scott G Nelson; Cheng Zhu; Xiaoqiang Shen
Journal:  J Am Chem Soc       Date:  2004-01-14       Impact factor: 15.419

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