Asymmetric Synthesis of Natural Products (eBook)

Ari M. P. Koskinen (Autor)

eBook Download: EPUB

2022 | 3. Auflage
384 Seiten
Wiley (Verlag)
978-1-119-70703-5 (ISBN)

Infos

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.

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.

Textauszug

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

...

Produkt-Details

• 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