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retrosynthetic analysis wikipedia jump to content main menu main menu move to sidebar hide navigation main page contents current events random article about wikipedia contact us contribute help learn to edit community portal recent changes upload file special pages search search appearance donate create account log in personal tools donate create account log in contents move to sidebar hide top 1 definitions 2 example 3 strategies toggle strategies subsection 3 1 functional group strategies 3 2 stereochemical strategies 3 3 structure goal strategies 3 4 transform based strategies 3 5 topological strategies 4 see also 5 references 6 external links toggle the table of contents retrosynthetic analysis 20 languages català čeština dansk deutsch español فارسی français עברית bahasa indonesia italiano 日本語 한국어 nederlands polski português русский türkçe українська 粵語 中文 edit links article talk english read edit view history tools tools move to sidebar hide actions read edit view history general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikimedia commons wikiquote wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia technique for solving problems in the planning of organic syntheses retrosynthetic analysis is a technique for solving problems in the planning of organic syntheses this is achieved by transforming a target molecule into simpler precursor structures regardless of any potential reactivity or interaction with reagents each precursor material is examined using the same method this procedure is repeated until simple or commercially available structures are reached these simpler or commercially available compounds can be used to form a synthesis of the target molecule retrosynthetic analysis was used as early as 1917 in robinson s total synthesis of tropinone 1 important conceptual work on retrosynthetic analysis was published by george vladutz in 1963 2 3 e j corey formalized and popularized the concept from 1967 onwards in his article general methods for the construction of complex molecules and his book the logic of chemical synthesis 4 5 6 7 the power of retrosynthetic analysis becomes evident in the design of a synthesis the goal of retrosynthetic analysis is a structural simplification often a synthesis will have more than one possible synthetic route retrosynthesis is well suited for discovering different synthetic routes and comparing them in a logical and straightforward fashion 8 a database may be consulted at each stage of the analysis to determine whether a component already exists in the literature in that case no further exploration of that compound would be required if that compound exists it can be a jumping off point for further steps developed to reach a synthesis there are academic and commercial groups developing retrosynthesis tools with the growing application of machine learning and artificial intelligence in chemistry many research groups such as the coley group from mit and companies such as chemical ai and reaxys have started to integrate deep learning into the conventional rule based approaches definitions edit disconnection a retrosynthetic step involving the breaking of a bond to form two or more synthons retron a minimal molecular substructure that enables certain transformations retrosynthetic tree a directed acyclic graph of several or all possible retrosyntheses of a single target synthon a fragment of a compound that assists in the formation of a synthesis derived from that target molecule a synthon and the corresponding commercially available synthetic equivalent are shown below target the desired final compound transform the reverse of a synthetic reaction the formation of starting materials from a single product example edit shown below is a retrosynthetic analysis of phenylacetic acid retrosynthetic analysis of phenylacetic acid in planning the synthesis two synthons are identified a nucleophilic cooh group and an electrophilic phch 2 group both synthons do not exist as written synthetic equivalents corresponding to the synthons are reacted to produce the desired product in this case the cyanide anion is the synthetic equivalent for the cooh synthon while benzyl bromide is the synthetic equivalent for the benzyl synthon the synthesis of phenylacetic acid determined by retrosynthetic analysis is thus phch 2 br nacn phch 2 cn nabr phch 2 cn 2 h 2 o phch 2 cooh nh 3 in fact phenylacetic acid has been synthesized from benzyl cyanide 9 itself prepared by the analogous reaction of benzyl bromide with sodium cyanide 10 strategies edit functional group strategies edit manipulation of functional groups can lead to significant reductions in molecular complexity stereochemical strategies edit numerous chemical targets have distinct stereochemical demands stereochemical transformations such as the claisen rearrangement and mitsunobu reaction can remove or transfer the desired chirality thus simplifying the target structure goal strategies edit directing a synthesis toward a desirable intermediate can greatly narrow the focus of analysis this allows bidirectional search techniques transform based strategies edit the application of transformations to retrosynthetic analysis can lead to powerful reductions in molecular complexity unfortunately powerful transform based retrons are rarely present in complex molecules and additional synthetic steps are often needed to establish their presence topological strategies edit the identification of one or more key bond disconnections may lead to the identification of key substructures or difficult to identify rearrangement transformations in order to identify the key structures disconnections that preserve ring structures are encouraged disconnections that create rings larger than 7 members are discouraged disconnection involves creativity see also edit organic synthesis total synthesis references edit robinson r 1917 lxiii a synthesis of tropinone journal of the chemical society transactions 111 762 768 doi 10 1039 ct9171100762 ugi ivar bauer johannes bley klemens dengler alf dietz andreas fontain eric gruber bernhard herges rainer knauer michael reitsam klaus stein natalie 1993 computer assisted solution of chemical problems the historical development and the present state of the art of a new discipline of chemistry angewandte chemie international edition in english 32 2 201 227 doi 10 1002 anie 199302011 vléduts g é 1963 concerning one system of classification and codification of organic reactions information storage and retrieval 1 2 3 117 146 doi 10 1016 0020 0271 63 90013 5 corey e j 1967 general methods for the construction of complex molecules pure and applied chemistry 14 19 38 doi 10 1351 pac196714010019 e j corey x m cheng 1995 the logic of chemical synthesis new york wiley isbn 978 0 471 11594 6 e j corey 1988 retrosynthetic thinking essentials and examples chem soc rev 17 111 133 doi 10 1039 cs9881700111 e j corey 1991 the logic of chemical synthesis multistep synthesis of complex carbogenic molecules nobel lecture reprint angewandte chemie international edition in english 30 5 455 465 doi 10 1002 anie 199104553 james law et al route designer a retrosynthetic analysis tool utilizing automated retrosynthetic rule generation journal of chemical information and modelling acs jcim publication date web february 6 2009 doi 10 1021 ci800228y http pubs acs org doi abs 10 1021 ci800228y wilhelm wenner 1963 phenylacetamide organic syntheses collected volumes vol 4 p 760 roger adams a f thal 1941 benzyl cyanide organic syntheses collected volumes vol 1 p 107 external links edit wikiquote has quotations related to retrosynthetic analysis chemairs ai driven retrosynthesis tools by chemical ai centre for molecular and biomolecular informatics archived february 12 2005 at the wayback machine presentation on archem route designer acs philadelphia september 2008 for more info on archem see the simbiosys pages manifold software freely available for academic users developed by postera archived january 13 2022 at the wayback machine retrosynthesis planning tool icsynth by infochem archived december 8 2017 at the wayback machine spaya software freely available proposed by iktos archived june 11 2023 at the wayback machine v t e chemical synthesis types artificial gene synthesis biomimetic synthesis bioretrosynthesis biosynthesis chemosynthesis convergent synthesis custom peptide synthesis direct process divergent synthesis electrosynthesis enantioselective synthesis fully automated synthesis hydrothermal synthesis lasis mechanosynthesis one pot synthesis organic synthesis peptide synthesis radiosynthesis retrosynthesis semisynthesis solid phase synthesis solvothermal synthesis total synthesis volume combustion synthesis category commons portal v t e branches of chemistry glossary of chemical formulae list of biomolecules list of inorganic compounds periodic table analytical calorimetry characterization chromatography gc hplc crystallography electroanalytical methods elemental analysis instrumental chemistry mass spectrometry ei icp maldi separation process spectroscopy ir raman uv vis nmr titration wet chemistry theoretical computational chemistry mathematical chemistry molecular modelling molecular mechanics molecular dynamics molecular geometry vsepr theory quantum chemistry physical chemical kinetics chemical physics molecular physics chemical thermodynamics cryochemistry electrochemistry spectroelectrochemistry photoelectrochemistry equilibrium chemistry femtochemistry interface and colloid science micromeritics mechanochemistry microwave chemistry photochemistry sonochemistry spectroscopy spin chemistry structural chemistry surface science thermochemistry inorganic ceramic chemistry cluster chemistry coordination chemistry magnetochemistry organometallic chemistry organolanthanide chemistry solid state chemistry organic dynamic covalent chemistry enantioselective synthesis fullerene chemistry organic reactions organic synthesis petrochemistry physical organic chemistry polymer chemistry retrosynthetic analysis stereochemistry alkane stereochemistry total synthesis semisynthesis biological biochemistry molecular biology cell biology bioinorganic chemistry bioorganic chemistry bioorganometallic chemistry biophysical chemistry chemical biology bioorthogonal chemistry clinical chemistry medicinal chemistry pharmacology neurochemistry interdisciplinarity nuclear chemistry radiochemistry radiation chemistry actinide chemistry cosmochemistry astrochemistry stellar chemistry geochemistry biogeochemistry photogeochemistry environmental chemistry atmospheric chemistry ocean chemistry clay chemistry carbochemistry food chemistry carbohydrate chemistry food physical chemistry agricultural chemistry soil chemistry chemistry education 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