Literature DB >> 17205179

Expedient total synthesis of pyrrothine natural products and analogs.

Thomas Hjelmgaard1, Michael Givskov, John Nielsen.   

Abstract

This paper describes an expedient and straightforward total synthesis of the two pyrrothine natural products holomycin (7 steps, 11% overall) and xenorhabdin I (7 steps, 11% overall) and analogs thereof via a common late-stage intermediate. The pathway proceeds via the pyrrothine hydrochloride intermediate (6 steps, 17% overall) which also gave access to very fast synthesis of analogs as demonstrated by the synthesis of , and (7 steps, 11-12% overall).

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Year:  2006        PMID: 17205179     DOI: 10.1039/b616411k

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  6 in total

1.  Enzymatic basis of "hybridity" in thiomarinol biosynthesis.

Authors:  Zachary D Dunn; Walter J Wever; Nicoleta J Economou; Albert A Bowers; Bo Li
Journal:  Angew Chem Int Ed Engl       Date:  2015-02-26       Impact factor: 15.336

2.  Novel hybrid-type antimicrobial agents targeting the switch region of bacterial RNA polymerase.

Authors:  Fumika Yakushiji; Yuko Miyamoto; Yuki Kunoh; Reiko Okamoto; Hidemasa Nakaminami; Yuri Yamazaki; Norihisa Noguchi; Yoshio Hayashi
Journal:  ACS Med Chem Lett       Date:  2013-01-11       Impact factor: 4.345

3.  A backup plan for self-protection: S-methylation of holomycin biosynthetic intermediates in Streptomyces clavuligerus.

Authors:  Bo Li; Ry R Forseth; Albert A Bowers; Frank C Schroeder; Christopher T Walsh
Journal:  Chembiochem       Date:  2012-10-24       Impact factor: 3.164

4.  Aldol reactions in multicomponent reaction based domino pathways: a multipurpose enabling tool in heterocyclic chemistry.

Authors:  Zhigang Xu; Fabio De Moliner; Alexandra P Cappelli; Christopher Hulme
Journal:  Org Lett       Date:  2013-05-29       Impact factor: 6.005

Review 5.  Dithiolopyrrolones: biosynthesis, synthesis, and activity of a unique class of disulfide-containing antibiotics.

Authors:  Bo Li; Walter J Wever; Christopher T Walsh; Albert A Bowers
Journal:  Nat Prod Rep       Date:  2014-07       Impact factor: 13.423

Review 6.  Dithiolopyrrolone natural products: isolation, synthesis and biosynthesis.

Authors:  Zhiwei Qin; Sheng Huang; Yi Yu; Hai Deng
Journal:  Mar Drugs       Date:  2013-10-17       Impact factor: 5.118

  6 in total

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