**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

carboxylic substitution

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

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

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

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,

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 exercisealiphatic 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

carboxylic substitution

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

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

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

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

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.

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Structure & Reactivity in Organic, Biological and Inorganic Chemistry

Send corrections to cschaller@csbsju.edu

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