Asymmetric Synthesis of Natural Products (eBook)
384 Seiten
Wiley (Verlag)
978-1-119-70703-5 (ISBN)
Fully updated learning resource covering the concept of using natural product chemistry for strategies in asymmetric synthesis
The third edition of Asymmetric Synthesis of Natural Products introduces students to the rapidly growing field of natural products in organic chemistry, discussing the practical, mainly pharmacological, importance of selected compounds and emphasizing the target-oriented approach of organic synthesis which is key in industrial strategies. To aid in reader comprehension, the text includes key references and an Index of Compounds.
The textbook is based on two lecture courses (Asymmetric Synthesis & Asymmetric Synthesis of Natural Products), which the author has delivered more than 50 times over the past 20 years in Finland, the UK, Italy, and Greece. This third edition is fully updated from the earlier versions (published by Wiley in 1993 and 2012). The importance of natural products as truly renewable raw materials in sustainable chemistry and circular economy is illustrated through applications of e.g. organocatalysis, organometallic catalysis, and biocatalysis. The contents consist of traditional text supplemented with illustrations (such as chemical drawings and structural formulae). Three dimensional aspects are also discussed with the use of 3D renderings of structures for both reaction mechanisms (molecular modeling) and crystallographic data.
Sample topics covered in the textbook include:
- The foundations of asymmetric synthesis, including the theory and applications of individual asymmetric reactions
- Sustainable development, the circular economy, and use of renewable raw materials that have become prominent in many fields of science and technology
- Various natural product classes, including carbohydrates, amino acids, peptides, proteins, nucleosides, nucleotides, nucleic acids, and polyketides
- The properties of these natural product classes, including their structures, biosynthesis, and interrelationships, as well as examples of asymmetric syntheses and the practical value of these compounds
Asymmetric Synthesis of Natural Products is a comprehensive, authoritative, and up-to-date learning resource on the subject for advanced level undergraduate or early-stage graduate students. It is also useful for specialists already working in synthesis who wish to learn about asymmetric synthesis.
Professor Ari M. P. Koskinen is a lecturer and researcher in the Department of Chemistry at Aalto School of Chemical Technology in Finland. He serves on several editorial boards including Chemical Society Reviews. His research focuses on the development of novel synthetic methods capable of being transferred into (industrially) applicable synthetic technologies and construction of complex natural and non-natural compounds with multiple chiral centers in enantiopure form.
Asymmetric Synthesis of Natural Products Fully updated learning resource covering the concept of using natural product chemistry for strategies in asymmetric synthesis The third edition of Asymmetric Synthesis of Natural Products introduces students to the rapidly growing field of natural products in organic chemistry, discussing the practical, mainly pharmacological, importance of selected compounds and emphasizing the target-oriented approach of organic synthesis which is key in industrial strategies. To aid in reader comprehension, the text includes key references and an Index of Compounds. The textbook is based on two lecture courses (Asymmetric Synthesis & Asymmetric Synthesis of Natural Products), which the author has delivered more than 50 times over the past 20 years in Finland, the UK, Italy, and Greece. This third edition is fully updated from the earlier versions (published by Wiley in 1993 and 2012). The importance of natural products as truly renewable raw materials in sustainable chemistry and circular economy is illustrated through applications of e.g. organocatalysis, organometallic catalysis, and biocatalysis. The contents consist of traditional text supplemented with illustrations (such as chemical drawings and structural formulae). Three dimensional aspects are also discussed with the use of 3D renderings of structures for both reaction mechanisms (molecular modeling) and crystallographic data. Sample topics covered in the textbook include: The foundations of asymmetric synthesis, including the theory and applications of individual asymmetric reactions Sustainable development, the circular economy, and use of renewable raw materials that have become prominent in many fields of science and technology Various natural product classes, including carbohydrates, amino acids, peptides, proteins, nucleosides, nucleotides, nucleic acids, and polyketides The properties of these natural product classes, including their structures, biosynthesis, and interrelationships, as well as examples of asymmetric syntheses and the practical value of these compounds Asymmetric Synthesis of Natural Products is a comprehensive, authoritative, and up-to-date learning resource on the subject for advanced level undergraduate or early-stage graduate students. It is also useful for specialists already working in synthesis who wish to learn about asymmetric synthesis.
List of Common Abbreviations
- AA
- asymmetric aminohydroxylation
- Ac
- acetyl
- acac
- acetylacetonate
- Ad
- adamantyl
- AD
- asymmetic dihydroxylation
- Adoc
- adamantyloxycarbonyl
- AIBN
- azoisobutyronitrile
- Alloc or AOC
- allyloxycarbonyl
- An
- p‐anisyl
- anh.
- anhydrous
- aq.
- aqueous
- atm
- atmosphere
- ATP
- adenosine triphosphate
- AZADO
- 2‐azaadamantane N‐oxyl
- 9‐BBN
- 9‐borabicyclo[3.3.1]nonane
- BINAP
- 2,2′‐(bisphenylphosphino)‐1,1′‐binaphthyl
- BIPHEP
- biphenylphosphine
- bipy
- 2,2′‐bipyridine
- BMDA
- bromomagnesium diisopropylamide
- BMS
- borane‐dimethyl sulfide
- Bn
- benzyl
- BOC (or Boc)
- tert‐butoxycarbonyl
- BOM
- benzyloxymethyl
- BOP reagent
-
benzotriazol‐1‐yloxytris (dimethylamino)phosphonium hexafluorophosphate
- BOP‐Cl
- bis(2‐oxo‐3‐oxazolidinyl)phosphinic chloride
- Bt
- benzotriazol‐1‐yl
- n‐Bu
- n‐butyl
- s‐Bu
- sec‐butyl
- t‐Bu
- tert‐butyl
- Bz
- benzoyl
- 18C6
- 18‐crown‐6
- CA
- chloroacetyl
- CAL
- Candida antarctica lipase
- CAN
- ceric ammonium nitrate
- cat
- catalytic amount
- CB
- catecholborane
- CBS
- Corey‐Bakshi‐Shibata oxazaborolidine
- Cbz or Z
- benzyloxycarbonyl (carbobenzyloxy)
- CCK
- cholecystokinin
- CD
- circular dichroism
- CDI
- 1,1′‐carbonyldiimidazole
- cHex
- cyclohexyl
- CMPI
- 2‐chloro‐1‐methylpyridinium iodide
- Cod
- cyclooctadiene
- Cp
- cyclopentadienyl
- Cp*
- pentamethylcyclopentadienyl
- CSA
- camphorsulfonic acid
- Cy
- cyclohexyl
- DABCO
- 1,4‐diazabicyclo[2.2.2]octane
- DAIB
- 3‐exo‐(dimethylamino)isoborneol
- DAST
- diethylamino sulfur trifluoride
- dba
- dibenzylideneacetone
- DBAD
- di‐t‐butyl azodicarboxylate
- DBN
- 1,5‐diazabicyclo[4.3.0]non‐5‐ene
- DBU
- 1,8‐diazabicyclo[5.4.0]undec‐7‐ene
- DCC
- dicyclohexylcarbodiimide
- DDQ
- 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone
- DEAD
- diethyl azodicarboxylate
- DEIPS
- diethylisopropylsilyl
- DET
- diethyl tartrate
- DHP
- 3,4‐dihydro‐2H‐pyran
- DIAD
- diisopropyl azodicarboxylate
- DIBAL‐H
- diisobutylaluminum hydride
- DIOP
- 2,3‐O‐isopropylidene‐2,3‐dihydroxy‐1,4‐bis(diphenylphosphino)butane
- DIPAMP
- 1,2‐bis[(2‐methoxyphenyl)(phenylphosphino)ethane]
- DIPEA
- diisopropylethylamine (Hünig's base)
- DIPT
- diisopropyl tartrate
- DMA
- dimethylacetamide
- DMAD
- dimethyl azodicarboxylate
- DMAP
- 4‐N,N‐dimethylaminopyridine
- DME
- 1,2‐dimethoxyethane
- DMF
- N,N‐dimethylformamide
- DMP
- Dess‐Martin periodinane
- DMPU
- N,N′‐dimethylpropyleneurea
- DMS
- dimethyl sulfide
- DMSO
- dimethyl sulfoxide
- DMTr or DMT
- di‐(p‐methoxyphenyl)phenylmethyl or dimethoxytrityl
- DNP
- 2,4‐dinitrophenyl
- DNs
- 2,4‐dinitrobenzenesulfonyl
- DPIPS
- diphenylisopropylsilyl
- DPM or Dpm
- diphenylmethyl
- Dpp
- diphenylphosphinyl
- DPPA
- diphenylphosphoryl azide
- dppb
- 1,4‐bis(diphenylphosphino)butane
- dppe
- 1,2‐bis(diphenylphosphino)ethane
- dppf
- 1,1′‐bis(diphenylphosphanyl)ferrocene
- DTBMS
- di‐t‐butylmethylsilyl
- DTT
- dthiothreitol
- EDC or EDCI
- 1‐ethyl‐3‐(3‐dimethylaminopropyl)carbodiimide
- EDTA
- ethylenediaminetetraacetic acid
- EE
- 1‐ethoxyethyl
- Et
- ethyl
- Fmoc
- 9‐fluorenylmethoxycarbonyl
- HATU
- O‐(7‐azabenzotriazol‐1‐yl)‐N,N,N′,N′‐tetramethyluronium hexafluorophosphate
- HBTU
- O‐benzotriazol‐1‐yl‐N,N,N′,N′‐tetramethyluronium hexafluorophosphate
- HMDS
- hexamethyldisilazane
- HMPA
- hexamethylphosphoric triamide (Me2N)3P=O
- HMPT
- hexamethylphosphorous triamide (Me2N)3P
- HOAt
- 7‐aza‐1‐hydroxybenzotriazole
- HOBt
- 1‐hydroxybenzotriazole
- HOMO
- highest occupied molecular orbital
- IBX
- o‐iodoxybenzoic acid
- Im
- imidazole
- IPA
- isopropyl alcohol
- Ipc
- isopinocamphenyl
- (Ipc)2BH
- diisopinocampheylborane
- KAPA
- potassium 3‐aminopropyl amide
- KDA
- potassium diisopropylamide
- KHMDS
- potassium hexamethyldisilazide
- L‐Selectride
- lithium tri‐sec‐butylborohydride
- LA
- Lewis acid
- LAH
- lithium aluminum hydride
- LDA
- lithium diisopropylamide
- LDBB
- lithium 4,4′‐di‐t‐butylphenylide
- Lev
- levulinoyl
- LiTMP
- lithium 2,2,6,6‐tetramethylpiperidide
- LUMO
- lowest unoccupied molecular orbital
- Lut.
- 2,6‐lutidine
- MAD
- methoxyaluminiumbis(2,6.di‐t‐butyl‐4‐methylphenoxide)
- mCPBA
- m‐chloroperoxybenzoic acid
- Me
- methyl
- MEM
- methoxyethoxymethyl
- Mes
- mesityl or 2,4,6‐trimethylphenyl
- MMTr or MMT
- p‐methoxyphenyldiphenylmethyl or methoxytrityl
- MOM
- methoxymethyl
- MoOPH
- oxodiperoxymolybdenum(pyridine)hexamethyl‐phosphoramide
- MPM see PMB
- Ms
- mesyl (methanesulfonyl)
- MTBE
- t‐butyl methyl ether
- MTHP
- 4‐methoxytetrahydropyranyl
- MTM
- methythiomethyl
- MTPA
- α‐methoxy‐α‐trifluoromethylphenylacetic acid
- Mtr
- 2,3,6‐4‐methoxybenzenesulfonyl
- Mts
- 2,4,6‐trimethylbenzenesulfonyl or mesitylenesulfonyl
- NADH
- nicotinamide dinucleotide hydride
- NADPH
- nicotinamide adenine dinucleotide phosphate
- nbd
- norbornadiene
- NBS
- N‐bromosuccinimide
- NCS
- N‐chlorosuccinimide
- Ni(acac)2
- nickel acetylacetonate
- NIS
- N‐iodosuccinimide
- NMM
- N‐methylmorpholine
- NMMO or NMO
- N‐methylmorpholine N‐oxide
- NMP
- N‐methylpyrrolidinone
- Nosyl or Ns
- (2‐ or) 4‐nitrobenzenesulfonyl
- Nu
- nucleophile
- OBO
- 2,6,7‐trioxabicyclo[2.2.2]octyl
- OP, OPP
- pyrophosphate (in biosynthetic schemes)
- OTf
- trifluoromethanesulfonate
- PALP
- pyridoxal phosphate
- PCC
- pyridinium chlorochromate
- PDC
- pyridinium dichromate
- Pd2(dba)3
- tris(dibenzylideneacetone)dipalladium
- Pf
- 9‐phenylfluorenyl
- PG
- protecting group
- Ph
- phenyl
- Pht
- phthalimidyl
- Pim
- phthalimidomethyl
- Piv (or Pv)
- pivaloyl
- PLE
- porcine liver esterase
- PMB or MPM
- p‐methoxybenzyl
- PMP
- p‐methoxyphenyl
- PNB
- p‐nitrobenzyl
- POM
- 4‐pentenyloxymethyl (carbohydrates)
- POM
- pivaloyloxymethyl
- PPL
- porcine pancreatic lipase
- PPTS
- pyridinium p‐toluenesulfonate
- Pr
- propyl
- Proton sponge
- 1,8‐bis(dimethylamino)naphthalene
- PTSA
- p‐toluenesulfonic acid
- Pv
- pivaloyl
- Pyr
- pyridine
- Px or pixyl
- 9‐(9‐phenyl)xanthenyl
- RAMP
- (R)‐1‐Amino‐2‐methoxymethylpyrrolidine
- Red‐Al
- sodium dihydrobis(2‐methoxyethoxy) aluminate, see also Vitride
- SAMP
- (S)‐1‐Amino‐2‐methoxymethylpyrrolidine
- ...
| Erscheint lt. Verlag | 9.9.2022 |
|---|---|
| Sprache | englisch |
| Themenwelt | Naturwissenschaften ► Chemie |
| ISBN-10 | 1-119-70703-X / 111970703X |
| ISBN-13 | 978-1-119-70703-5 / 9781119707035 |
| Haben Sie eine Frage zum Produkt? |
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