Structure & Reactivity in Organic, Biological and Inorganic Chemistry by Chris Schaller is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported License.
Reactivity in Chemistry
Organic Synthesis
OS1. Road Maps in Total Synthesis of Natural Products
Topics required for successful completion are listed under each link.
alkene addition
carbonyl addition
carboxylic substitution
nucleophilic substitution
oxidation of alcohols
pericyclics
carbonyl addition
carbonyl reduction
"Claisen condensation"-type carboxylic substitution
cuprate addition
ester reduction
nitrile hydrolysis
alkene addition
carbonyl addition
elimination
pericyclics
aldol reaction
aliphatic nucleophilic substitution
carbonyl addition
carboxyl substitution
elimination
oxidation of alcohols
radicals
Aplykurodinone, Danishefsky, 2010
aliphatic nucleophilic substitution
carbonyl addition
carboxylic substitution
elimination
oxidation of alcohols
esterification & amidification
Michael addition
reduction of esters
Wittig & Horner-Wadsworth-Emmons reactions
aliphatic nucleophilic substitution
carbonyl addition
carboxylic substitution
Aza-epothilone B, Danishefsky, 2000
with bioassay study
aliphatic nucleophilic substitution
carbonyl addition
carboxylic substitution
(partial synthesis)
carbonyl addition, anionic & semianionic nucleophiles
carbonyl addition, aldols
carbonyl addition, ylides
aliphatic nucleophilic substitution
electrophilic addition to alkenes
carbonyl addition
nucleophilic addition to epoxide
aliphatic nucleophilic substitution
silyl protecting groups
carboxylic substitution
carbonyl addition
electrophilic addition to alkenes
ylide addition
oxidation of alcohols
dihydroxylation
Horner-Wadsworth-Emmons or Wittig reaction
hydroboration - oxidation
oxidation of alcohols
reduction of esters and ketones
ring-closing olefin metathesis
Callipeltoside, MacMillan, 2008
aliphatic nucleophilic substitution
electrophilic addition to alkenes
carbonyl addition
carboxylic substitution
oxidation of alcohols
aliphatic nucleophilic substitution
carbonyl addition
carboxylic substitution
Diels Alder
etherification
palladium coupling
Wittig or Tebbe reactions
aliphatic nucleophilic substitution and elimination
Deoxytetracycline, Stork, 1996
carbonyl addition (anionic and neutral nucleophiles)
carboxylic substitution
conjugate addition
Dedihydrosemofalin, Overman, 2003
alpha-alkylation
aza-Cope rearrangement
catalytic hydrogenation
Diels Alder
iminium ion formation
oxidation of alcohols
ozonolysis
reduction of esters
silylation of alcohols
silylation of enolates
silyl ether cleavage
Wittig & Horner-Wadsorth-Emmons reactions
carbonyl addition
carboxylic substitution
aliphatic nucleophilic substitution
electrophilic addition to alkenes
aliphatic nucleophilic substitution
alkene oxidation
carbonyl addition
carboxylic substitution
elimination
oxidation of alcohols
pericyclics
aliphatic nucleophilic substitution
carbonyl addition
carboxylic substitution
aldol reaction
alpha deprotonation
Grignard reactions
Wittig and Horner-Wadsworth-Emmons reactions
aliphatic nucleophilic substitution
carbonyl addition,
carboxylic substitution,
electrophilic addition to alkenes
oxidation of alcohols
radicals
aliphatic nucleophilic substitution
carbonyl addition
carboxylic substitution
conjugate addition
electrophilic addition to alkenes
enolates
rearrangements
radicals
Glucosylceramide, Overkleeft, 2007
contains a bioassay exercise
aliphatic nucleophilic substitution
carbonyl addition
carboxylic substitution
elimination
oxidation of alcohols
Juvenile Hormone 1, Corey, 1968
aliphatic nucleophilic substitution
carbonyl addition
carboxylic substitution
cuprate addition
electrophilic addition to alkenes
oxidation of alcohols
Wittig reaction
Lepistine, Yokoshima & Fukuyama, 2014
aliphatic nucleophilic substitution
elimination
aliphatic nucleophilic substitution
alkene oxidation
carbonyl addition
carboxylic substitution
elimination
oxidation of alcohols
acetal/ketal cleavage
acetal/ketal formation
catalytic hydroformylation of alkenes
Grignard reactions
reductive amination
carboxylic substitution: esterification and amidification
conjugate addition
acetal / ketal formation
alkene reduction
carbonyl reduction
cuprate addition
Diels Alder reaction
epoxide opening (organometallic)
ester hydrolysis
keto-enol tautomerism
methoxymethyl ether formation
olefin metathesis
silyl ether formation & cleavage
syn dihydroxylation
thioacetal / thioketal cleavage
aliphatic nucleophilic substitution
carbonyl addition
carboxylic substitution
conjugate addition
elimination
oxidation of alcohols
Norzoanthamine, Theodorakis, 2011
Robinson annulation
conjugate addition
anionic addition to carbonyls
carboxylic substitution
alkene reduction
epoxidation
hydroboration / oxidation
Lindlar's catalyst
silyl ether cleavage
aldol condensation
aliphatic nucleophilic substitution
carbonyl addition
carboxylic substitution
elimination
oxidation of alcohols
pericyclics
Perhydrohistrionicotoxin, Corey, 1975
aliphatic nucleophilic substitution
carbonyl addition
carboxylic substitution
conjugate addition
elimination
enolates
oxidation of alcohols
radicals
aldol condensation
aliphatic nucleophilic substitution
carbonyl addition
carboxylic substitution,
elimination
oxidation of alcohols
pericyclics
aliphatic nucleophilic substitution
electrophilic addition to alkenes
electrophilic addition to alkenes: halogenation, hydroboration, oxymercuration, epoxidation, cyclopropanation
aliphatic nucleophilic substitution
epoxidation
epoxide ring-opening
esterification
oxidation of alcohols
silyl ether cleavage
aliphatic nucleophilic substitution
carbonyl addition
carboxylic substitution
elimination
oxidation of alcohols
aliphatic nucleophilic substitution
carbonyl addition
carboxylic substitution
carbonyl addition
carboxylic substitution
carbonyl addition
carboxylic substitution
Contains a bioassay exercise.
aliphatic nucleophilic substitution
carbonyl addition
carboxylic substitution
electrophilic addition to alkenes
oxidation of alcohols
aliphatic nucleophilic substitution
carbonyl addition
carboxylic substitution,
Serotobenine, Fukuyama & Kan, 2008
aliphatic nucleophilic substitution
alkene oxidation
carbonyl addition
carboxylic substitution
elimination
oxidation of alcohols
pericyclics
aliphatic nucleophilic substitution
alkene oxidation
carbonyl addition
carboxylic substitution
elimination
oxidation of alcohols
activation of carboxylic acids
esterification & amidification
Grignard reactions
hydrolysis of amides
reduction of esters
Wittig & Horner-Wadsworth-Emmons reactions
aliphatic nucleophilic substitution
alkene oxidation
carbonyl addition
carboxylic substitution
conjugate addition
elimination
enolates
Exercise: catalytic cycles in transition metal organometallics.
aldol condensation
alpha alkylation
conjugate addition
electrophilic aromatic substitution
etherification
palladium coupling
aliphatic nucleophilic substitution
alkene oxidation
carbonyl addition
carboxylic substitution
elimination
oxidation of alcohols
pericyclics
radicals
aliphatic nucleophilic substitution
alkene oxidation
carbonyl addition
carboxylic substitution
electrophilic addition to alkenes
oxidation of alcohols
pericyclics
rearrangements
carbonyl addition
carboxylic substitution, aldol
carbonyl addition, anionic & semianionic nucleophiles
carbonyl addition, aldols
carbonyl addition, ylides
carbonyl addition
carboxylic substitution
addition to carbonyl (organometallic)
allylic substitution
ester hydrolysis
ester reduction
esterification
ether formation
Mitsunobu reaction
silyl ether formation and cleavage
Wittig / Horner-Wadsworth-Emmons
acetals & ketals
Claisen rearrangement
Diels Alder
syn-dihydroxylations
esterification
Grignard reagents
hydride additions
oxidation of alcohols
silyl ethers
Aliphatic nucleophilic substitution
Zaragozic acid, Nicolaou, 1994
aliphatic nucleophilic substitution
alkene oxidation
carbonyl addition
carboxylic substitution
organo-transition metal reactions
oxidation of alcohols
radicals
sulfur ylides
aliphatic nucleophilic substitution
electrophilic addition to alkenes
This site is written and maintained by Chris P. Schaller, Ph.D., College of Saint Benedict / Saint John's University (with contributions from other authors as noted). It is freely available for educational use.
Structure & Reactivity in Organic, Biological and Inorganic Chemistry by Chris Schaller is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported License.
Send corrections to cschaller@csbsju.edu
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