title: Lessons and revelations from biomimetic syntheses.
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.
authors.affiliation: Department of Biochemistry, The University of Texas Southwestern Medical Center at Dallas, Dallas, Texas, USA.
authors.forename: Mina
authors.initials: M
authors.lastname: Razzak
authors.forename: Jef K
authors.initials: JK
authors.lastname: De Brabander
mesh_terms: D040761:Biomimetic Materials / Q000138:chemical synthesis* / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D015394:Molecular Structure; D013237:Stereoisomerism
references.citation: J Am Chem Soc. 2010 Sep 15;132(36):12733-40
references.pmid: 20722388
references.citation: Nat Prod Rep. 2008 Apr;25(2):254-97
references.pmid: 18389138
references.citation: Chem Commun (Camb). 2011 Jan 7;47(1):427-9
references.pmid: 20848010
references.citation: Angew Chem Int Ed Engl. 2010 Feb 1;49(6):1095-8
references.pmid: 20041464
references.citation: Angew Chem Int Ed Engl. 2007;46(35):6721-4
references.pmid: 17685369
references.citation: Angew Chem Int Ed Engl. 2007;46(13):2254-6
references.pmid: 17304611
references.citation: J Am Chem Soc. 2009 Mar 25;131(11):3834-5
references.pmid: 19292484
references.citation: Angew Chem Int Ed Engl. 2007;46(13):2320-4
references.pmid: 17318930
references.citation: Angew Chem Int Ed Engl. 2007;46(13):2262-5
references.pmid: 17304610
references.citation: J Org Chem. 2010 May 7;75(9):2785-9
references.pmid: 20359229
references.citation: Chembiochem. 2003 Aug 4;4(8):713-5
references.pmid: 12898620
references.citation: Angew Chem Int Ed Engl. 2011 Apr 4;50(15):3362-74
references.pmid: 21413105
references.citation: J Am Chem Soc. 2009 May 13;131(18):6383-5
references.pmid: 19385615
references.citation: Molecules. 2011 Jan 21;16(1):951-69
references.pmid: 21258300
references.citation: Angew Chem Int Ed Engl. 2007;46(35):6586-94
references.pmid: 17724780
references.citation: Org Lett. 2006 Oct 12;8(21):4907-10
references.pmid: 17020333
references.citation: Nat Prod Rep. 1988 Apr;5(2):129-45
references.pmid: 3145474
references.citation: Chem Soc Rev. 2009 Nov;38(11):3175-92
references.pmid: 19847350
references.citation: J Am Chem Soc. 2007 May 16;129(19):6336-42
references.pmid: 17455936
references.citation: Nat Prod Rep. 2008 Apr;25(2):401-26
references.pmid: 18389143
references.citation: Angew Chem Int Ed Engl. 2008;47(44):8450-4
references.pmid: 18816540
references.citation: Chem Rev. 2005 Dec;105(12):4314-47
references.pmid: 16351046
references.citation: Biopolymers. 2010 Sep;93(9):755-63
references.pmid: 20577995
references.citation: Mar Drugs. 2008 May 07;6(2):73-102
references.pmid: 18728761
references.citation: Angew Chem Int Ed Engl. 2007;46(43):8186-91
references.pmid: 17890663
references.citation: Nature. 2011 May 5;473(7345):109-12
references.pmid: 21544146
references.citation: Nat Prod Rep. 2011 Feb;28(2):411-28
references.pmid: 21170424
references.citation: Science. 2007 Aug 31;317(5842):1189-92
references.pmid: 17761875
references.citation: Angew Chem Int Ed Engl. 2011 Apr 18;50(17):3882-7
references.pmid: 21472917
references.citation: Chemistry. 2002 Oct 4;8(19):4346-53
references.pmid: 12355522
references.citation: J Am Chem Soc. 2009 May 20;131(19):6678-9
references.pmid: 19402635
references.citation: Nat Chem Biol. 2008 Sep;4(9):535-7
references.pmid: 18677305
references.citation: Org Lett. 2009 Mar 19;11(6):1297-300
references.pmid: 19281134
references.citation: Angew Chem Int Ed Engl. 2009;48(7):1283-6
references.pmid: 19140150
references.citation: J Nat Prod. 2008 Dec;71(12):2064-7
references.pmid: 19053517
references.citation: Angew Chem Int Ed Engl. 2003 Jul 14;42(27):3078-115
references.pmid: 12866094
references.citation: Nat Prod Rep. 2007 Oct;24(5):931-48
references.pmid: 17898890
references.citation: J Org Chem. 2011 Jun 3;76(11):4221-59
references.pmid: 21438619
references.citation: Angew Chem Int Ed Engl. 2008;47(19):3573-7
references.pmid: 18389509
references.citation: Nature. 2009 Jun 11;459(7248):824-8
references.pmid: 19440196
references.citation: Org Biomol Chem. 2008 Dec 21;6(24):4483-93
references.pmid: 19039353
references.citation: J Am Chem Soc. 2007 Oct 24;129(42):12896-900
references.pmid: 17902668
references.citation: Chem Rev. 2010 Feb 10;110(2):932-48
references.pmid: 19769330
references.citation: Toxicon. 2001 Jan;39(1):97-106
references.pmid: 10936626
references.citation: Chem Rev. 2005 Dec;105(12):4757-78
references.pmid: 16351061
references.citation: Org Lett. 2008 Jun 19;10(12):2533-6
references.pmid: 18505261
references.citation: Nat Rev Cancer. 2009 Jun;9(6):445-52
references.pmid: 19461669
references.citation: J Am Chem Soc. 2006 Dec 20;128(50):16046-7
references.pmid: 17165752
references.citation: Angew Chem Int Ed Engl. 2007;46(13):2257-61
references.pmid: 17304609
references.citation: J Org Chem. 2006 Jul 7;71(14):5357-60
references.pmid: 16808526
references.citation: Toxicon. 1985;23(3):473-9
references.pmid: 3895583
references.citation: Annu Rev Microbiol. 1999;53:411-46
references.pmid: 10547697
references.citation: Mar Drugs. 2010 Mar 19;8(3):763-809
references.pmid: 20411125
references.citation: Nature. 2008 Jan 24;451(7177):417-24
references.pmid: 18216847
references.citation: J Nat Prod. 2010 Aug 27;73(8):1438-40
references.pmid: 20795742
references.citation: Science. 2007 Nov 2;318(5851):783-7
references.pmid: 17975062
references.citation: Angew Chem Int Ed Engl. 2004 May 10;43(20):2674-7
references.pmid: 18629987
references.citation: Angew Chem Int Ed Engl. 2006 Jun 19;45(25):4126-30
references.pmid: 16703636
references.citation: J Am Chem Soc. 2007 Apr 18;129(15):4762-75
references.pmid: 17375928
references.citation: Proc Natl Acad Sci U S A. 1996 Dec 10;93(25):14323-7
references.pmid: 8962049
references.citation: Chem Soc Rev. 2009 Nov;38(11):3242-72
references.pmid: 19847354
references.citation: Nat Prod Rep. 2000 Aug;17(4):349-66
references.pmid: 11014337
references.citation: Angew Chem Int Ed Engl. 2004 Jan;43(2):160-81
references.pmid: 14695603
references.citation: Angew Chem Int Ed Engl. 2009;48(29):5250-81
references.pmid: 19572302
references.citation: Chem Rev. 2005 Dec;105(12):4730-56
references.pmid: 16351060
references.citation: J Am Chem Soc. 2009 Feb 11;131(5):1753-65
references.pmid: 19143488
references.citation: J Am Chem Soc. 2011 Feb 16;133(6):1902-8
references.pmid: 21235230
references.citation: J Org Chem. 2007 Mar 30;72(7):2309-17
references.pmid: 17315930
references.citation: Nat Chem Biol. 2007 Jul;3(7):396-407
references.pmid: 17576427
references.citation: J Am Chem Soc. 2009 Aug 19;131(32):11350-2
references.pmid: 19722648