Literature DB >> 22086288

Lessons and revelations from biomimetic syntheses.

Mina Razzak1, Jef K De Brabander.   

Abstract

Biomimetic synthesis describes the field of organic chemistry that aims to emulate the natural, biosynthetic processes toward natural products. As well as providing insight into how molecules are formed in nature, the benefits of this approach to total synthesis are numerous and extend beyond the gains typical of traditional synthesis. For example, using biosynthetic proposals to design a synthetic route can highlight alternative methods to the desired target. The pursuit of biomimetic syntheses also promotes the development of new reactions to prove or disprove a biosynthetic proposal or to unravel mechanistic implications of a proposed biosynthesis and can lead to the identification of new natural products. Here we look at some recent compelling examples and examine how biomimetic synthesis has led to the discovery of new procedures and principles that would not have been found by other approaches.

Mesh:

Year:  2011        PMID: 22086288     DOI: 10.1038/nchembio.709

Source DB:  PubMed          Journal:  Nat Chem Biol        ISSN: 1552-4450            Impact factor:   15.040


  70 in total

Review 1.  Chemistry and biology of biosynthetic Diels-Alder reactions.

Authors:  Emily M Stocking; Robert M Williams
Journal:  Angew Chem Int Ed Engl       Date:  2003-07-14       Impact factor: 15.336

2.  Berkelic acid, a novel spiroketal with selective anticancer activity from an acid mine waste fungal extremophile.

Authors:  Andrea A Stierle; Donald B Stierle; Kal Kelly
Journal:  J Org Chem       Date:  2006-07-07       Impact factor: 4.354

3.  Notoamides F-K, prenylated indole alkaloids isolated from a marine-derived Aspergillus sp.

Authors:  Sachiko Tsukamoto; Hikaru Kato; Masayuki Samizo; Yuka Nojiri; Hiroyuki Onuki; Hiroshi Hirota; Tomihisa Ohta
Journal:  J Nat Prod       Date:  2008-12       Impact factor: 4.050

Review 4.  If C-H bonds could talk: selective C-H bond oxidation.

Authors:  Timothy Newhouse; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2011-03-16       Impact factor: 15.336

5.  Revisiting the Kinnel-Scheuer hypothesis for the biosynthesis of palau'amine.

Authors:  Zhiqiang Ma; Jianming Lu; Xiao Wang; Chuo Chen
Journal:  Chem Commun (Camb)       Date:  2010-09-16       Impact factor: 6.222

Review 6.  Convergent strategies for the total synthesis of polycyclic ether marine metabolites.

Authors:  Makoto Sasaki; Haruhiko Fuwa
Journal:  Nat Prod Rep       Date:  2008-01-17       Impact factor: 13.423

7.  Total synthesis of eudesmane terpenes by site-selective C-H oxidations.

Authors:  Ke Chen; Phil S Baran
Journal:  Nature       Date:  2009-05-13       Impact factor: 49.962

Review 8.  Hydrocarbon hydroxylation by cytochrome P450 enzymes.

Authors:  Paul R Ortiz de Montellano
Journal:  Chem Rev       Date:  2010-02-10       Impact factor: 60.622

Review 9.  Epoxide-opening cascades in the synthesis of polycyclic polyether natural products.

Authors:  Ivan Vilotijevic; Timothy F Jamison
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

10.  A concise synthesis of berkelic acid inspired by combining the natural products spicifernin and pulvilloric acid.

Authors:  Christopher F Bender; Francis K Yoshimoto; Christopher L Paradise; Jef K De Brabander
Journal:  J Am Chem Soc       Date:  2009-08-19       Impact factor: 15.419

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  19 in total

1.  Natural products: Emulation illuminates biosynthesis.

Authors:  Jaron A M Mercer; Noah Z Burns
Journal:  Nat Chem       Date:  2015-11       Impact factor: 24.427

Review 2.  Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products.

Authors:  Zachary G Brill; Matthew L Condakes; Chi P Ting; Thomas J Maimone
Journal:  Chem Rev       Date:  2017-03-15       Impact factor: 60.622

3.  Gold(I)-Mediated Cycloisomerization/Cycloaddition Enables Bioinspired Syntheses of Neonectrolides B-E and Analogues.

Authors:  Thomas J Purgett; Matthew W Dyer; Bryce Bickel; James McNeely; John A Porco
Journal:  J Am Chem Soc       Date:  2019-09-12       Impact factor: 15.419

4.  Enantioselective synthesis of an ophiobolin sesterterpene via a programmed radical cascade.

Authors:  Zachary G Brill; Huck K Grover; Thomas J Maimone
Journal:  Science       Date:  2016-05-27       Impact factor: 47.728

5.  Natural products as inspiration for the development of new synthetic methods.

Authors:  Zhiqiang Ma; Chuo Chen
Journal:  J Chin Chem Soc       Date:  2017-08-09       Impact factor: 1.967

Review 6.  Revealing nature's synthetic potential through the study of ribosomal natural product biosynthesis.

Authors:  Kyle L Dunbar; Douglas A Mitchell
Journal:  ACS Chem Biol       Date:  2013-01-08       Impact factor: 5.100

7.  Asymmetric Induction via a Helically Chiral Anion: Enantioselective Pentacarboxycyclopentadiene Brønsted Acid-Catalyzed Inverse-Electron-Demand Diels-Alder Cycloaddition of Oxocarbenium Ions.

Authors:  Chirag D Gheewala; Jennifer S Hirschi; Wai-Hang Lee; Daniel W Paley; Mathew J Vetticatt; Tristan H Lambert
Journal:  J Am Chem Soc       Date:  2018-03-06       Impact factor: 15.419

8.  Gold(I)-catalyzed formation of bicyclo[4.2.0]oct-1-enes.

Authors:  Ryan J Felix; Osvaldo Gutierrez; Dean J Tantillo; Michel R Gagné
Journal:  J Org Chem       Date:  2013-05-13       Impact factor: 4.354

Review 9.  Total synthesis of complex terpenoids employing radical cascade processes.

Authors:  Kevin Hung; Xirui Hu; Thomas J Maimone
Journal:  Nat Prod Rep       Date:  2018-02-21       Impact factor: 13.423

10.  A biosynthetically inspired synthesis of (-)-berkelic acid and analogs.

Authors:  Christopher F Bender; Christopher L Paradise; Vincent M Lynch; Francis K Yoshimoto; Jef K De Brabander
Journal:  Tetrahedron       Date:  2018-01-12       Impact factor: 2.457

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