Literature DB >> 31518120

A Biomimetic Synthesis Elucidates the Origin of Preuisolactone A.

Alexander J E Novak1, Claire E Grigglestone1, Dirk Trauner1.   

Abstract

A short, biomimetic synthesis of the fungal metabolite preuisolactone A is described. Its key steps are a purpurogallin-type (5 + 2)-cycloaddition, followed by fragmentation, vinylogous aldol addition, oxidative lactonization, and a final benzilic acid rearrangement. Our work explains why preuisolactone A has been isolated as a racemate and suggests that the natural product is not a sesquiterpenoid but a phenolic polyketide.

Entities:  

Year:  2019        PMID： 31518120      PMCID： PMC7249536          DOI： 10.1021/jacs.9b08892

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  22 in total

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Authors:  Kun Zhao; Gui-Juan Cheng; Hongzhi Yang; Hai Shang; Xinhao Zhang; Yun-Dong Wu; Yefeng Tang
Journal:  Org Lett       Date:  2012-09-04       Impact factor: 6.005

2.  Total synthesis of kingianins A, D, and F.

Authors:  Samuel L Drew; Andrew L Lawrence; Michael S Sherburn
Journal:  Angew Chem Int Ed Engl       Date:  2013-03-06       Impact factor: 15.336

3.  Novel lignans from a Cinnamomum sp. from Bougainville.

Authors:  G C Brophy; J Mohandas; M Slaytor; S Sternhell; T R Watson; L A Wilson
Journal:  Tetrahedron Lett       Date:  1969-12       Impact factor: 2.415

4.  Biomimetic total synthesis of santalin Y.

Authors:  Sebastian Strych; Guillaume Journot; Ryan P Pemberton; Selina C Wang; Dean J Tantillo; Dirk Trauner
Journal:  Angew Chem Int Ed Engl       Date:  2015-04-08       Impact factor: 15.336

5.  Biomimetic one-step access to nitraramine from simple C5 units. Revision of the previously reported structure of epinitraramine to nitraramine.

Authors:  Edmond Gravel; Erwan Poupon; Reynald Hocquemiller
Journal:  Org Lett       Date:  2005-06-09       Impact factor: 6.005

6.  Paracaseolide A, first α-alkylbutenolide dimer with an unusual tetraquinane oxa-cage bislactone skeleton from Chinese mangrove Sonneratia paracaseolaris.

Authors:  Xue-Lian Chen; Hai-Li Liu; Jia Li; Guo-Rong Xin; Yue-Wei Guo
Journal:  Org Lett       Date:  2011-08-29       Impact factor: 6.005

7.  Incarvilleatone, a new cyclohexylethanoid dimer from Incarvillea younghusbandii and its inhibition against nitric oxide (NO) release.

Authors:  Yan-Ping Gao; Yun-Heng Shen; Shou-De Zhang; Jun-Mian Tian; Hua-Wu Zeng; Ji Ye; Hui-Liang Li; Lei Shan; Wei-Dong Zhang
Journal:  Org Lett       Date:  2012-04-06       Impact factor: 6.005

8.  ortho-Quinone methides from para-quinones: total synthesis of rubioncolin B.

Authors:  Jean-Philip Lumb; Kevin C Choong; Dirk Trauner
Journal:  J Am Chem Soc       Date:  2008-06-27       Impact factor: 15.419

9.  An eight-step synthesis of epicolactone reveals its biosynthetic origin.

Authors:  Pascal Ellerbrock; Nicolas Armanino; Marina K Ilg; Robert Webster; Dirk Trauner
Journal:  Nat Chem       Date:  2015-09-07       Impact factor: 24.427

Review 10.  Synthesis of Theaflavins and Their Functions.

Authors:  Masumi Takemoto; Hiroaki Takemoto
Journal:  Molecules       Date:  2018-04-16       Impact factor: 4.411
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  5 in total

Review 1.  Recent Advances in Biocatalysis for Drug Synthesis.

Authors:  Alina Kinner; Philipp Nerke; Regine Siedentop; Till Steinmetz; Thomas Classen; Katrin Rosenthal; Markus Nett; Jörg Pietruszka; Stephan Lütz
Journal:  Biomedicines       Date:  2022-04-21

Review 2.  Natural Product Synthesis Enabled by Domino Processes Incorporating a 1,2-Rearrangement Step.

Authors:  Bastien Delayre; Qian Wang; Jieping Zhu
Journal:  ACS Cent Sci       Date:  2021-04-08       Impact factor: 14.553

3.  Stereoselective Synthesis of Cyclobutanes by Contraction of Pyrrolidines.

Authors:  Chunngai Hui; Lukas Brieger; Carsten Strohmann; Andrey P Antonchick
Journal:  J Am Chem Soc       Date:  2021-11-08       Impact factor: 15.419

4.  Cloning and Functional Characterization of the Polyketide Synthases Based on Genome Mining of Preussia isomera XL-1326.

Authors:  Qingpei Liu; Dan Zhang; Yao Xu; Shuaibiao Gao; Yifu Gong; Xianhua Cai; Ming Yao; Xiaolong Yang
Journal:  Front Microbiol       Date:  2022-05-04       Impact factor: 5.640

5.  Total Synthesis of (-)-Mitrephorone A Enabled by Stereoselective Nitrile Oxide Cycloaddition and Tetrasubstituted Olefin Synthesis.

Authors:  Michael Schneider; Matthieu J R Richter; Erick M Carreira
Journal:  J Am Chem Soc       Date:  2020-10-06       Impact factor: 15.419
  5 in total

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