Lessons from the synthetic chemist nature

Natural Product Reports
Gerrit JürjensDavid A Candito

Abstract

This conceptual review examines the ideal multistep synthesis from the perspective of nature. We suggest that besides step- and redox economies, one other key to efficiency is steady state processing with intermediates that are immediately transformed to the next intermediate when formed. We discuss four of nature's strategies (multicatalysis, domino reactions, iteration and compartmentation) that commonly proceed via short-lived intermediates and show that these strategies are also part of the chemist's portfolio. We particularly focus on compartmentation which in nature is found microscopically within cells (organelles) and between cells and on a molecular level on multiprotein scaffolds (e.g. in polyketide synthases) and demonstrate how compartmentation is manifested in modern multistep flow synthesis.

References

Feb 22, 1979·Nature·P B SchiffS B Horwitz
Feb 1, 1996·Nature Structural Biology·J StauntonP F Leadlay
Dec 1, 1995·Microbiology·H C Lynch, M E Bushell
Feb 1, 1996·Chemical Reviews·Lutz F. Tietze
May 16, 2002·Natural Product Reports·Paul M Dewick
May 29, 2003·Chemistry & Biology·A Kassem El-SayedChristopher M Thomas
Dec 26, 2003·Angewandte Chemie·María C de la Torre, Miguel A Sierra
Jul 24, 2004·Chemical Society Reviews·Ji Min LeeSukbok Chang
Sep 11, 2004·Journal of Psychopharmacology·Gavin P Reynolds
Mar 10, 2005·Chemical Reviews·Julia-Christina WasilkeGuillermo C Bazan
Dec 3, 2005·Nature Reviews. Microbiology·Kira J Weissman, Peter F Leadlay
Dec 18, 2007·Journal of the American Chemical Society·Suk Joong LeeMartin D Burke
Dec 28, 2007·Accounts of Chemical Research·Paul A WenderThomas H Pillow
Apr 5, 2008·Natural Product Reports·Paul G BulgerRodolfo Marquez
Sep 10, 2008·The Journal of Organic Chemistry·Dieter Enders, Arun A Narine
Nov 28, 2008·Journal of the American Chemical Society·Jeremy M RichterPhil S Baran
Mar 19, 2009·Angewandte Chemie·Noah Z BurnsReinhard W Hoffmann
Jul 10, 2009·Nature·Paul A Wender, Benjamin L Miller
Oct 8, 2009·Angewandte Chemie·Andrew R BogdanD Tyler McQuade
Mar 2, 2010·Nature Reviews. Microbiology·Christopher M ThomasThomas J Simpson
Mar 17, 2010·Angewandte Chemie·Brian J Albert, Hisashi Yamamoto
Apr 2, 2010·Natural Product Reports·Hui ZhouYi Tang
May 6, 2010·Journal of the American Chemical Society·Eric M WoerlyMartin D Burke
Jun 15, 2010·The Journal of Organic Chemistry·Tanja Gaich, Phil S Baran
Nov 17, 2010·Nature Reviews. Microbiology·Jason M Crawford, Craig A Townsend
Mar 4, 2011·Angewandte Chemie·Brian J AlbertHisashi Yamamoto
Mar 17, 2011·Chemical Communications : Chem Comm·Jens WegnerAndreas Kirschning
Jan 1, 2010·Topics in Current Chemistry·Alexandra A RobertsTobias A M Gulder
May 5, 2011·Natural Product Reports·Dean J Tantillo
Jun 18, 2011·Angewandte Chemie·Seiko FujiiMartin D Burke
Nov 17, 2011·Nature Chemical Biology·Mina Razzak, Jef K De Brabander
Feb 7, 2012·Natural Product Reports·Barbara T UeberbacherKurt Faber
Aug 22, 2012·Natural Product Reports·Yang GaoReuben J Peters
Mar 8, 2013·Journal of the American Chemical Society·Xin GaoMichael J Krische
Jul 22, 2014·Natural Product Reports·Mikail E Abbasov, Daniel Romo

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Citations

Jan 26, 2016·Chemistry : a European Journal·Jan Hartwig, Andreas Kirschning
Nov 4, 2015·Journal of Industrial Microbiology & Biotechnology·Christopher C Ladner, Gavin J Williams
Jul 21, 2015·Angewandte Chemie·Jan Hartwig, Andreas Kirschning
Dec 4, 2019·Angewandte Chemie·Vincent C FäsekeChristof Sparr
Jun 3, 2020·Chembiochem : a European Journal of Chemical Biology·Friederike WesemannAndreas Kirschning
Feb 19, 2020·Natural Product Reports·Vanessa HarmsJeroen S Dickschat
Sep 4, 2020·Journal of Industrial Microbiology & Biotechnology·Alexandra A MalicoGavin J Williams
May 14, 2021·Organic Letters·Conrad Kuhwald, Andreas Kirschning
Jun 28, 2016·Tetrahedron·Heriberto RiveraMichael D Burkart

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