Reactivity in Chemistry

Organic Synthesis

OS1.  Road Maps in Total Synthesis of Natural Products

Topics required for successful completion are listed under each link.

Abyssomicin, Sorensen, 2006

alkene addition

carbonyl addition

carboxylic substitution

nucleophilic substitution

oxidation of alcohols

 pericyclics

Amphilectolide, Trauner, 2014

carbonyl addition

carboxylic substitution

Annamoxic Acid, Corey, 2004

 alkene addition

carbonyl addition

elimination

 pericyclics

Anominine, Nicolaou, 2012

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

Aurantioclavine, Ellman, 2010

aliphatic nucleophilic substitution

carbonyl addition

carboxylic substitution

Aza-epothilone B, Danishefsky, 2000

with bioassay study

aliphatic nucleophilic substitution

carbonyl addition

carboxylic substitution

Brevenal, Crimmins, 2010

(partial synthesis)

carbonyl addition, anionic & semianionic nucleophiles

carbonyl addition, aldols

carbonyl addition, ylides

Brevetoxin, Crimmins, 2009

aliphatic nucleophilic substitution

electrophilic addition to alkenes

carbonyl addition

Briarellin, Crimmins, 2011

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

Cassiol, Stoltz, 2008

aliphatic nucleophilic substitution

carbonyl addition

carboxylic substitution

Cavicularin, Beaudry, 2013

Diels Alder

etherification

 palladium coupling

Wittig or Tebbe reactions

Clavolonine, Fujioka, 2011

aliphatic nucleophilic substitution and elimination

Deoxytetracycline, Stork, 1996

carbonyl addition (anionic and neutral nucleophiles)

carboxylic substitution

conjugate addition

Dendrobine, Carreira, 2012

carbonyl addition

carboxylic substitution

Doliculide, Ghosh, 2001

aliphatic nucleophilic substitution

electrophilic addition to alkenes

Dynemicin, Danishefsky, 1996

aliphatic nucleophilic substitution

alkene oxidation

carbonyl addition

carboxylic substitution

elimination

oxidation of alcohols

 pericyclics

Echinopine, Nicolaou, 2010

aliphatic nucleophilic substitution

carbonyl addition

carboxylic substitution,

Fischerindole, Baran, 2008

aliphatic nucleophilic substitution

 carbonyl addition,

carboxylic substitution,

electrophilic addition to alkenes

oxidation of alcohols

radicals

Ginkgolide, Corey, 1988

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

Longifolene, Corey, 1961

aliphatic nucleophilic substitution

alkene oxidation

carbonyl addition

carboxylic substitution

elimination

oxidation of alcohols

Manzacidin A, Kawabata, 2013

carboxylic substitution

Nakadomarin, Kerr, 2007

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

Octalactin, Buszek, 1994

 

 Okilactomycin, Smith, 2007

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

 

Periplanone, Still, 1979

aldol condensation

aliphatic nucleophilic substitution

carbonyl addition

carboxylic substitution,

elimination

oxidation of alcohols

pericyclics

Platensimicin, Ghosh, 2009

aliphatic nucleophilic substitution

electrophilic addition to alkenes

Polyanthellin, Johnson, 2009

electrophilic addition to alkenes: halogenation, hydroboration, oxymercuration, epoxidation, cyclopropanation

aliphatic nucleophilic substitution

Prostaglandin A2, Corey, 1972

 aliphatic nucleophilic substitution

carbonyl addition

carboxylic substitution

elimination

oxidation of alcohols

Quinine, Stork, 2001

aliphatic nucleophilic substitution

carbonyl addition

carboxylic substitution

Quinocarcin, Stoltz, 2008

carbonyl addition

carboxylic substitution

Salvileucalin, Reisman, 2011

carbonyl addition

carboxylic substitution

Saxitoxin, Du Bois, 2006

Contains a bioassay exercise.

aliphatic nucleophilic substitution

carbonyl addition

carboxylic substitution

electrophilic addition to alkenes

oxidation of alcohols

Scholarisine, Smith, 2012

 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

Solamine, Stark, 2006

 aliphatic nucleophilic substitution

alkene oxidation

carbonyl addition

carboxylic substitution

elimination

oxidation of alcohols

Strychnine, Overman, 1993

aliphatic nucleophilic substitution

alkene oxidation

carbonyl addition

carboxylic substitution

conjugate addition

 elimination

enolates

Exercise: catalytic cycles in transition metal organometallics.

Taiwaniaquinol, Fillion, 2005

aldol condensation

alpha alkylation

conjugate addition

electrophilic aromatic substitution

etherification

palladium coupling

Taxol, Nicolaou, 1994

aliphatic nucleophilic substitution

alkene oxidation

carbonyl addition

carboxylic substitution

elimination

oxidation of alcohols

pericyclics

radicals

Tetrodotoxin, Kishi, 1972

aliphatic nucleophilic substitution

alkene oxidation

carbonyl addition

carboxylic substitution

electrophilic addition to alkenes

oxidation of alcohols

pericyclics

rearrangements

Tubingensin, Li, 2012

carbonyl addition

carboxylic substitution, aldol

Tulearin, Cossy, 2009

carbonyl addition, anionic & semianionic nucleophiles

carbonyl addition, aldols

carbonyl addition, ylides

Vermiculine, Corey, 1975

carbonyl addition

carboxylic substitution

Vibsanin, Takeo, 2015

 

Vinigrol, Berriault, 2005

acetals & ketals

Claisen rearrangement

Diels Alder

syn-dihydroxylations

esterification

Grignard reagents

hydride additions

oxidation of alcohols

silyl ethers

Vittatalactone, Breit, 2010

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

Zincophorin, Hsung, 2007

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 by Chris Schaller is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported License

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