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Chemistry LibreTexts

Roadmap Problems in Natural Product synthesis

Topics required for successful completion are listed under each link.

Abbysomicin, Sorensen, 2006

Carbonyl addition, Carboxylic substitution, Oxidation, Nucleophilic substitution, Alkene addition, Pericyclics

Annamoxic Acid, Corey, 2004

Carbonyl addition, Elimination, Alkene addition, Pericyclics

Anominine, Nicolaou, 2012

Carbonyl Addition, Aldol, Carboxyl Substitution, Oxidation, Nucleophilic Substitution, Elimination, Radicals

Aplykurodinone, Danishefsky, 2010

Carbonyl addition, Carboxylic substitution, Oxidation, Nucleophilic Substitution & Elimination

Aza-epothilone B, Danishefsky, 2000

Carbonyl addition, Carboxylic substitution, Nucleophilic Substitution, Bioassay study

Callipeltoside, MacMillan, 2008

Carbonyl addition, Carboxylic substitution, Oxidation, Nucleophilic substitution, Alkene addition

Dendrobine, Carreira, 2012

Carbonyl addition, Carboxylic substitution

Dynemicin, Danishefsky, 1996

Carbonyl addition, Carboxylic substitution, Nucleophilic substitution & elimination, Oxidation, Alkene oxidation, Pericyclics

Echinopine, Nicolaou, 2010

Carbonyl addition, Carboxylic substitution, Nucleophilic Substitution

Fischerindole, Baran, 2008

Carbonyl addition, Carboxylic substitution, Oxidation, Nucleophilic substitution, Alkene addition, Radicals

Ginkgolide, Corey, 1988

Carbonyl addition, Conjugate addition, Enolates, Carboxylic substitution, Nucleophilic substitution, Alkene addition, Rearrangements, Radicals

Glucosylceramide, Overkleeft, 2007

Carbonyl addition, Carboxylic substitution, Oxidation, Nucleophilic Substitution & Elimination

Contains a bioassay exercise.

Histrionicotoxin, Corey, 1975

Carbonyl addition, Carboxylic substitution, Aldol & Claisen, A-lpha-alkylation, Conjugate addition, Oxidation, Nucleophilic Substitution & Elimination

Juvenile Hormone 1, Corey, 1968

Carbonyl addition, Phosphorus ylides, Carboxylic substitution, Oxidation, Nucleophilic substitution, Cuprate addition, Alkene addition

Longifolene, Corey, 1961

Carbonyl addition, Carboxylic substitution, Oxidation, Nucleophilic Substitution & Elimination, Alkene oxidation

Nakadomarin, Kerr, 2007

Carbonyl addition, Conjugate addition, Carboxylic substitution, Oxidation, Nucleophilic Substitution & Elimination

Okilactomycin, Smith, 2007

Carbonyl addition, Aldols, Carboxylic substitution, Oxidation, Nucleophilic Substitution & Elimination,  Pericyclics

Perhydrohistrionicotoxin, Corey, 1975

Carbonyl addition, Enolates, Conjugate addition, Carboxylic substitution, Oxidation, Nucleophilic substitution & elimination, Radicals

Periplanone, Still, 1979

Carbonyl addition, Aldols, Carboxylic substitution, Oxidation, Nucleophilic Substitution & Elimination,  Pericyclics

Prostaglandin A2, Corey, 1972

Carbonyl addition, Carboxylic substitution, Oxidation, Nucleophilic Substitution & Elimination

Quinine, Stork, 2001

Carbonyl addition, Carboxylic substitution, Nucleophilic Substitution

Quinocarcin, Stoltz, 2008

Carbonyl addition, Carboxylic substitution

Salvileucalin, Reisman, 2011

Carbonyl addition, Carboxylic substitution

Saxitoxin, Du Bois, 2006

Carbonyl addition, Carboxylic substitution, Oxidation, Nucleophilic Substitution, Alkene addition

Contains a bioassay exercise.

Serotobenine, Fukuyama & Kan, 2008

Carbonyl addition, Carboxylic substitution, Oxidation, Nucleophilic Substitution & Elimination, Alkene oxidation, Pericyclics

Solamine, Stark, 2006

Carbonyl addition, Carboxylic substitution, Oxidation, Nucleophilic Substitution & Elimination, Alkene oxidation

Strychnine, Overman, 1993

Carbonyl addition, Enolates, Conjugate addition, Carboxylic substitution, Nucleophilic substitution & elimination, Alkene oxidation

Exercise: catalytic cycles in transition metal organometallics.

Taxol, Nicolaou, 1994

Carbonyl addition, Carboxylic substitution, Oxidation, Nucleophilic substitution & elimination, Alkene oxidation, Pericyclics, Radicals

Tubingensin, Li, 2012

Carbonyl addition, Carboxylic substitution, Aldol

Tetrodotoxin, Kishi, 1972

Carbonyl addition, Carboxylic substitution, Oxidation, Nucleophilic substitution, Alkene addition, Alkene oxidation, Pericyclics, Rearrangements

Zaragozic acid, Nicolaou, 1994

Carbonyl addition, Carboxylic Substitution, Sulfur ylides, Oxidation, Nucleophilic substitution, Alkene oxidation, Radicals, Organo-transition metal reactions

Zincophorin, Hsung, 2007

Nucleophilic Substitution, Alkene addition