Literature DB >> 23146096

A macrocyclic approach to tetracycline natural products. Investigation of transannular alkylations and Michael additions.

Joseph S Wzorek1, Thomas F Knöpfel, Ioannis Sapountzis, David A Evans.   

Abstract

A new approach to the tetracycline core structure is presented. The pivotal intermediate is identified as macrocycle III. The two interior bonds (C4a-C12a and C5a-C11a) are to be constructed through sequential transannular Michael additions (III-II) and compression-promoted transannular isoxazole alkylations from intermediate II.

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Year:  2012        PMID： 23146096     DOI： 10.1021/ol302691j

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


  3 in total

1.  Total synthesis and structural revision of viridicatumtoxin B.

Authors:  K C Nicolaou; Christian Nilewski; Christopher R H Hale; Heraklidia A Ioannidou; Abdelatif ElMarrouni; Lizanne G Koch
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-24       Impact factor: 15.336

2.  Total synthesis of viridicatumtoxin B and analogues thereof: strategy evolution, structural revision, and biological evaluation.

Authors:  K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou; Abdelatif ElMarrouni; Lizanne G Nilewski; Kathryn Beabout; Tim T Wang; Yousif Shamoo
Journal:  J Am Chem Soc       Date:  2014-08-15       Impact factor: 15.419

3.  Transgenic Strategies for Sparse but Strong Expression of Genetically Encoded Voltage and Calcium Indicators.

Authors:  Chenchen Song; Quyen B Do; Srdjan D Antic; Thomas Knöpfel
Journal:  Int J Mol Sci       Date:  2017-07-07       Impact factor: 5.923
  3 in total

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