Literature DB >> 20196572

Aryne acyl-alkylation in the general and convergent synthesis of benzannulated macrolactone natural products: an enantioselective synthesis of (-)-curvularin.

Pamela M Tadross1, Scott C Virgil, Brian M Stoltz.   

Abstract

A general approach for the synthesis of benzannulated macrolactone natural products utilizing an aryne acyl-alkylation reaction is described. Toward this end, the total syntheses of the natural products (-)-curvularin, curvulin, and (-)-diplodialide C are reported. Furthermore, the aryne insertion technology has enabled the rapid conversion of simple diplodialide natural products to curvularin, thereby connecting these two biosynthetically distinct classes of compounds via synthetic methods.

Entities:  

Mesh:

Substances:

Year:  2010        PMID: 20196572     DOI: 10.1021/ol100335y

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


  6 in total

Review 1.  Recent progress regarding the bioactivities, biosynthesis and synthesis of naturally occurring resorcinolic macrolides.

Authors:  Jing Xu; Cheng-shi Jiang; Zai-long Zhang; Wen-quan Ma; Yue-wei Guo
Journal:  Acta Pharmacol Sin       Date:  2014-01-27       Impact factor: 6.150

2.  Comparison of 10,11-Dehydrocurvularin Polyketide Synthases from Alternaria cinerariae and Aspergillus terreus Highlights Key Structural Motifs.

Authors:  Rachel V K Cochrane; Zhizeng Gao; Gareth R Lambkin; Wei Xu; Jaclyn M Winter; Sandra L Marcus; Yi Tang; John C Vederas
Journal:  Chembiochem       Date:  2015-10-23       Impact factor: 3.164

3.  Three-component coupling reactions of arynes for the synthesis of benzofurans and coumarins.

Authors:  Eito Yoshioka; Shigeru Kohtani; Hideto Miyabe
Journal:  Molecules       Date:  2014-01-13       Impact factor: 4.411

4.  An efficient synthesis of 4-phenoxy-quinazoline, 2-phenoxy-quinoxaline, and 2-phenoxy-pyridine derivatives using aryne chemistry.

Authors:  Mahesh K Zilla; Sheena Mahajan; Rajni Khajuria; Vivek K Gupta; Kamal K Kapoor; Asif Ali
Journal:  RSC Adv       Date:  2021-01-15       Impact factor: 3.361

5.  Triple Aryne-Tetrazine Reaction Enabling Rapid Access to a New Class of Polyaromatic Heterocycles.

Authors:  Sung-Eun Suh; Stephanie A Barros; David M Chenoweth
Journal:  Chem Sci       Date:  2015       Impact factor: 9.825

6.  Total synthesis of the antitumor antibiotic (±)-streptonigrin: first- and second-generation routes for de novo pyridine formation using ring-closing metathesis.

Authors:  Timothy J Donohoe; Christopher R Jones; Anne F Kornahrens; Luiz C A Barbosa; Louise J Walport; Matthew R Tatton; Michael O'Hagan; Akshat H Rathi; David B Baker
Journal:  J Org Chem       Date:  2013-12-12       Impact factor: 4.354

  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.