Online citations, reference lists, and bibliographies.
← Back to Search

The Economies Of Synthesis.

T. Newhouse, P. Baran, R. W. Hoffmann
Published 2009 · Chemistry, Medicine

Save to my Library
Download PDF
Analyze on Scholarcy Visualize in Litmaps
Share
Reduce the time it takes to create your bibliography by a factor of 10 by using the world’s favourite reference manager
Time to take this seriously.
Get Citationsy
In this tutorial review the economies of synthesis are analysed from both detailed and macroscopic perspectives, using case-studies from complex molecule synthesis. Atom, step, and redox economy are more than philosophical constructs, but rather guidelines, which enable the synthetic chemist to design and execute an efficient synthesis. Students entering the field of synthesis might find this tutorial helpful for understanding the subtle differences between these economic principles and also see real-world situations where such principles are put into practice.
This paper references
10.1021/JA00853A023
Systematic synthesis design. IV. Numerical codification of construction reactions
J. B. Hendrickson (1975)
10.1016/S0040-4020(01)93261-2
Further synthetic studies on rifamycin s
H. Nagaoka (1981)
10.1016/S0040-4039(00)88675-X
Synthetic studies on arene-olefin cycloadditions -III- total synthesis of (±)-hirsutene☆
P. Wender (1982)
10.1001/jama.1982.03330140068043
The Enchanted Ring: The Untold Story of Penicillin
H. Neu (1982)
10.1021/JA00363A025
Total synthesis of (±)-pentalenene, the least oxidized neutral triquinane metabolite of Streptomyces griseochromogenes
L. A. Paquette (1983)
10.1021/JA00272A046
A general approach to linearly fused triquinane natural products: total syntheses of (±)-hirsutene, (±)-coriolin, and (±)-capnellene
G. Mehta (1986)
10.1246/CL.1987.1259
Stereoselective syntheses of (+)-davanone and (+)-artemone via anti-selective epoxidation and iodo-cyclization.
Y. Honda (1987)
10.1021/JA00201A038
Total Synthesis of Palytoxin Carboxylic Acid and Palytoxin Amide
R. Armstrong (1989)
The Logic of Chemical Synthesis
E. Corey (1989)
10.1126/science.248.4962.1532
Biomimetic Total Synthesis of Proto-Daphniphylline
S. Piettre (1990)
10.1126/SCIENCE.1962206
The atom economy--a search for synthetic efficiency.
B. Trost (1991)
10.1002/ANGE.19921040604
Die faszinierenden Alkaloide aus Yuzuriha
C. Heathcock (1992)
10.1021/JO00032A004
A highly convergent asymmetric synthesis of the C(19)-C(27) segment of rifamycin S: an application of enantiodifferentiating acetalization with menthone
T. Harada (1992)
10.1021/JA00071A069
Singlet oxygen oxidation of bipyrroles: total synthesis of d,l- and meso-isochrysohermidin
H. Wasserman (1993)
10.1021/AR00037A002
TWO-DIRECTIONAL CHAIN SYNTHESIS AND TERMINUS DIFFERENTIATION
Christopher S. Poss (1994)
10.1021/JA00090A050
CONCISE SYNTHESIS OF ()-PEROVSKONE
G. Majetich (1994)
10.1021/JA00103A065
Synthesis of Palytoxin from Palytoxin Carboxylic Acid
E. Suh (1994)
10.1016/0040-4020(94)01070-G
Two-directional synthesis and its use in natural product synthesis
S. Magnuson (1995)
10.1016/0040-4039(95)02132-9
Stereoselective synthesis of the C- and CD-ring systems of hemibrevetoxin B
T. Nakata (1996)
10.1021/JO971863M
Application of Newly Developed Anti-Selective Aldol Methodology: Synthesis of C6−C13 and C19−C28 Fragments of Miyakolide
T. Yoshimitsu (1997)
10.1021/OL9905046
A convenient method for synthesis of enantiomerically enriched methylphenidate from N-methoxycarbonylpiperidine.
Y. Matsumura (1999)
10.1002/(SICI)1521-3757(20000103)112:1<46::AID-ANGE46>3.0.CO;2-P
Der Stand der Totalsynthese zu Beginn des 21. Jahrhunderts
K. Nicolaou (2000)
10.1021/JA005552W
Total Synthesis of (±)-Torreyanic Acid
Chaomin Li (2000)
10.1002/1521-3757(20010702)113:13<2543::AID-ANGE2543>3.0.CO;2-E
Totalsynthese von Colombiasin A
K. C. Nicolaou (2001)
10.1002/1521-3757(20020617)114:12<2298::AID-ANGE2298>3.0.CO;2-B
Total synthesis of the amaryllidaceae alkaloid (+)-plicamine and its unnatural enantiomer by using solid-supported reagents and scavengers in a multistep sequence of reactions.
I. Baxendale (2002)
10.1021/OL020208K
A highly abbreviated synthesis of pentalenene by means of the squarate ester cascade.
L. Paquette (2002)
10.1021/OL035380I
A synthesis of (+)-salvadione-A.
G. Majetich (2003)
10.1021/JO026456B
Desymmetrization of a centrosymmetric diepoxide: efficient synthesis of a key intermediate in a total synthesis of hemibrevetoxin B.
Joanne M. Holland (2003)
10.1016/J.BMCL.2003.12.097
Synthesis of methylphenidate analogues and their binding affinities at dopamine and serotonin transport sites.
H. Davies (2004)
10.1021/OP0302107
Research and Development of a Second-Generation Process for Oseltamivir Phosphate, Prodrug for a Neuraminidase Inhibitor
P. Harrington (2004)
10.1021/JA048808X
Simple, catalytic enantioselective syntheses of estrone and desogestrel.
Qi-Ying Hu (2004)
10.1056/NEJMRA050740
Neuraminidase inhibitors for influenza.
A. Moscona (2005)
10.1021/JA056206N
Synthesis of (−)-Quinocarcin by Directed Condensation of α-Amino Aldehydes
Soojin Kwon (2005)
10.1002/ANIE.200462215
Chasing a phantom by total synthesis: the butylcycloheptylprodigiosin case.
A. Fürstner (2005)
10.1021/CEN-V083N036.P016
SPECTROSCOPY'S NEW ERA
Amanda Yarnell (2005)
10.1021/OL051403C
Toward the synthesis of spirastrellolide a: construction of a tetracyclic C26-C40 subunit containing the DEF-bis-spiroacetal.
I. Paterson (2005)
10.1021/OL047800P
Hydrocarbon oxidation vs C-C bond-forming approaches for efficient syntheses of oxygenated molecules.
K. J. Fraunhoffer (2005)
10.1002/ANIE.200503678
Total synthesis of (+)-rugulosin and (+)-2,2'-epi-cytoskyrin A through cascade reactions.
K. Nicolaou (2005)
10.1016/J.TET.2006.02.085
New reactions and step economy: the total synthesis of (±)-salsolene oxide based on the type II transition metal-catalyzed intramolecular [4 + 4] cycloaddition
P. Wender (2006)
10.1021/JA0616433
A short enantioselective pathway for the synthesis of the anti-influenza neuramidase inhibitor oseltamivir from 1,3-butadiene and acrylic acid.
Ying-Yeung Yeung (2006)
10.1002/ANGE.200601872
Kaskadenreaktionen in der Totalsynthese
K. Nicolaou (2006)
10.1021/JA056877L
Combined C-H activation/cope rearrangement as a strategic reaction in organic synthesis: total synthesis of (-)-colombiasin a and (-)-elisapterosin B.
H. Davies (2006)
10.1039/B612697A
Synthesis of the DEF-bis-spiroacetal of spirastrellolide A exploiting a double asymmetric dihydroxylation/spiroacetalisation strategy.
I. Paterson (2006)
10.1055/S-2006-950311
Protecting-group-free synthesis
R. W. Hoffmann (2006)
10.1021/CR078380V
Innovations and green chemistry.
I. Horvat́h (2007)
10.1021/CR0783784
Introduction: Green chemistry
I. Horváth (2007)
10.1021/JO070871S
Pattern recognition in retrosynthetic analysis: snapshots in total synthesis.
R. M. Wilson (2007)
10.1002/ANIE.200605058
Total Synthesis of Paecilomycine A
S. Min (2007)
10.1002/ANIE.200701552
Total synthesis and revised structure of biyouyanagin A.
K. Nicolaou (2007)
10.1002/ANGE.200801441
Eine kurze Formalsynthese von (−)-Platencin†
K. Tiefenbacher (2008)
10.1002/anie.200705565
Total synthesis of spirastrellolide A methyl ester--part 1: Synthesis of an advanced C17-C40 bis-spiroacetal subunit.
I. Paterson (2008)
10.1021/AR700155P
Function-oriented synthesis, step economy, and drug design.
P. Wender (2008)
10.1002/anie.200705566
Total synthesis of spirastrellolide A methyl ester--part 2: Subunit union and completion of the synthesis.
I. Paterson (2008)
10.1002/anie.200802912
High-pressure entry into platencin.
Dennis C. J. Waalboer (2008)
10.1002/ANGE.200705303
Synthese von Platensimycin
K. Tiefenbacher (2008)
10.1002/anie.200800756
Total synthesis of (+/-)-platencin.
Joji Hayashida (2008)
Molecules That Changed TheWorld, Wiley-VCH
K. C. Nicolaou (2008)
10.1021/jo9001855
A nine-step total synthesis of (-)-platencin.
K. Tiefenbacher (2009)
10.1021/OP800157Z
Global Green Chemistry Metrics Analysis Algorithm and Spreadsheets: Evaluation of the Material Efficiency Performances of Synthesis Plans for Oseltamivir Phosphate (Tamiflu) as a Test Case
J. Andraos (2009)
10.1038/nchem.216
Protecting-group-free synthesis as an opportunity for invention.
I. S. Young (2009)
10.1002/anie.200804883
High-yielding synthesis of the anti-influenza neuramidase inhibitor (-)-oseltamivir by three "one-pot" operations.
H. Ishikawa (2009)
10.1038/460197a
Synthesis at the molecular frontier
P. Wender (2009)
10.1021/ol900697w
A concise, biomimetic total synthesis of (+)-davanone.
K. C. Morrison (2009)
10.1002/ANGE.200806086
Redoxkonomie in der organischen Synthese
N. Burns (2009)
10.1021/cr800449m
Synthetic approaches to the neuraminidase inhibitors zanamivir (Relenza) and oseltamivir phosphate (Tamiflu) for the treatment of influenza.
J. Magano (2009)
10.1021/ar800182r
Chemoselectivity: the mother of invention in total synthesis.
R. A. Shenvi (2009)



This paper is referenced by
10.1515/PSR-2018-0096
Stereoselective organocascades: from fundamentals to recent developments
E. Massolo (2021)
10.1021/ACSCATAL.0C05260
Hydroalkylation of Alkenes with 1,3-Diketones via Gold(III) or Silver(I) Catalysis: Divergent Mechanistic Pathways Revealed by a DFT-Based Investigation
M. Jalali (2021)
10.1016/J.TET.2021.132141
Total synthesis of LC-KA05, the proposed structure of LC-KA05-2, and 2,18-seco-lankacidinol B: A quest to revisit lankacidin biosynthesis
Kuan Zheng (2021)
10.1039/d1sc03037j
Multicomponent syntheses of 5- and 6-membered aromatic heterocycles using group 4–8 transition metal catalysts
Daniel N Huh (2021)
10.1039/d1cc01048d
Advances in transition metal-free deborylative transformations of gem-diborylalkanes.
W. Jo (2021)
10.1039/d1ob00795e
Sequential condensation/biannulation reactions of β-(2-aminophenyl)-α,β-ynones with 1,3-dicarbonyls.
Vincenzo Marsicano (2021)
10.1039/d0np00086h
Balancing skeleton and functional groups in total syntheses of complex natural products: a case study of tigliane, daphnane and ingenane diterpenoids.
Zhi Liu (2021)
10.1002/ADSC.202100181
Triflic Acid‐Catalyzed Chemo‐ and Site‐Selective C−H Bond Functionalization of Phenols With 1,3‐Dienes
Zhenlin Liu (2021)
10.1039/D0NJ05078D
Innovation of hypervalent(iii) iodine in the synthesis of natural products
Zhuo Wang (2021)
10.1039/D1GC00049G
Visible-light-induced oxidative coupling of vinylarenes with diselenides leading to α-aryl and α-alkyl selenomethyl ketones
Gong-Qing Liu (2021)
10.1002/HLCA.202000198
Mono‐Gold(I)‐Catalyzed Enantioselective Intermolecular Reaction of Ynones with Styrenes: Tandem Diels–Alder and Ene Sequence
M. Nanko (2021)
10.3390/CATAL11060712
Asymmetric Catalytic Ketimine Mannich Reactions and Related Transformations
Changgong Xu (2021)
10.1039/d0re00273a
Evolution of flow-oriented design strategies in the continuous preparation of pharmaceuticals
Zsolt Fülöp (2020)
10.1021/acs.jnatprod.0c00310
Synthesis of (-)-Melodinine K: A Case Study of Efficiency in Natural Product Synthesis.
Manish Walia (2020)
10.1002/cssc.202000317
A Glimpse on Green Chemistry Practices in the Pharmaceutical Industry.
Sudripet Sharma (2020)
10.1002/anie.202000743
Photoredox-Catalyzed Isomerization of Highly-Substituted Allylic Alcohols via C-H bond activation.
Kai Guo (2020)
10.1080/14712598.2021.1846714
An overview of process development for antibody-drug conjugates produced by chemical conjugation technology
Yutaka Matsuda (2020)
10.1002/ejoc.201901495
Lewis Base Catalysis Promoted Nucleophilic Substitutions – Recent Advances and Future Directions
P. Huy (2020)
10.1002/CJOC.202000432
Catalytic Asymmetric Mannich‐Type Reaction Enabled by Efficient Dienolization of α, β‐Unsaturated Pyrazoleamides†
Hai-Jun Zhang (2020)
10.1002/slct.202003097
α‐Cyclopiazonic Acid from Synthesis Perspective
Mushtaq Ahmad (2020)
10.1039/c9cs00346k
Deconjugated butenolide: a versatile building block for asymmetric catalysis.
Abhijnan Ray Choudhury (2020)
10.1002/slct.202001822
Insight into Temperature Dependency and Design of Experiments towards Process Development for Cysteine‐Based Antibody‐Drug Conjugates
Yutaka Matsuda (2020)
10.1002/anie.202009490
Redox-Neutral TEMPO Catalysis Toward Direct Radical (Hetero)Aryl C-H Di- and Trifluoromethoxylation.
Johnny W Lee (2020)
10.1039/c9np00071b
Engineering biosynthetic enzymes for industrial natural product synthesis.
Stephanie Galanie (2020)
10.1021/acs.accounts.0c00477
Palladium-Catalyzed Asymmetric Allylic C-H Functionalization: Mechanism, Stereo- and Regioselectivities, and Synthetic Applications.
Pu-Sheng Wang (2020)
10.1002/ejoc.201901170
Cobaloxime‐Catalyzed Hydrogen Evolution in Photoredox‐Facilitated Small‐Molecule Functionalization
Kaitie C. Cartwright (2020)
10.1039/d0cc00265h
Palladium-catalyzed diastereo- and enantioselective allylic alkylation of oxazolones with 1,3-dienes under base-free conditions.
Hai-Jian Yang (2020)
10.1039/d0py00346h
Alkene–azide chemistry: a facile, one-step, solvent- and catalyst-free approach for developing new functional monomers and polymers
S. Santra (2020)
10.1002/chem.202001952
Photoredox/Cobalt Dual Catalyzed Decarboxylative Elimination of Carboxylic Acids: Development and Mechanistic Insight.
Kaitie C. Cartwright (2020)
10.1002/asia.202000134
Non-Heme-Type Ruthenium Catalyzed Chemo- and Site-Selective C-H Oxidation.
Daiki Doiuchi (2020)
10.1021/acscatal.0c03343
Redox-Triggered Ruthenium-Catalyzed Remote C–H Acylation with Primary Alcohols
Xiao Guo (2020)
10.1016/j.gresc.2020.11.001
Synthesis of tetrahydropyrrolothiazoles through one-pot and four-component N,S-acetalation and decarboxylative [3+2] cycloaddition
Xiaoming Ma (2020)
See more
Semantic Scholar Logo Some data provided by SemanticScholar