Literature DB >> 15704914

A short total synthesis of aureothin and N-acetylaureothamine.

Mikkel F Jacobsen1, John E Moses, Robert M Adlington, Jack E Baldwin.   

Abstract

The total synthesis of the nitrophenyl pyrones, (+/-)-aureothin and (+/-)-N-acetylaureothamine, starting from known 2-ethyl-6-methoxy-3,5-dimethyl-4H-pyran-4-one are described. The key steps involved in the synthesis are the construction of the tetrahydrofuran motif using a palladium-catalyzed cycloaddition and the ruthenium-catalyzed cross-metathesis reaction of an alkenyl boronic ester. [reaction: see text]

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Year:  2005        PMID: 15704914     DOI: 10.1021/ol047594l

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


  3 in total

1.  Alkyne elementometalation-Pd-catalyzed cross-coupling. Toward synthesis of all conceivable types of acyclic alkenes in high yields, efficiently, selectively, economically, and safely: "green" way.

Authors:  Ei-Ichi Negishi; Guangwei Wang; Honghua Rao; Zhaoqing Xu
Journal:  J Org Chem       Date:  2010-05-21       Impact factor: 4.354

2.  Total synthesis and evaluation of iso-duocarmycin SA and iso-yatakemycin.

Authors:  Karen S MacMillan; Trinh Nguyen; Trihn Nguyen; Inkyu Hwang; Dale L Boger
Journal:  J Am Chem Soc       Date:  2009-01-28       Impact factor: 15.419

3.  Potent inhibition of HIV replication in primary human cells by novel synthetic polyketides inspired by Aureothin.

Authors:  Alexander Herrmann; Manfred Roesner; Thomas Werner; Stefanie M Hauck; Alisha Koch; Amelie Bauer; Martha Schneider; Ruth Brack-Werner
Journal:  Sci Rep       Date:  2020-01-28       Impact factor: 4.379

  3 in total

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