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  3. Chemistry 411: Chemistry and Synthesis of Natural Products

Chemistry 411: Chemistry and Synthesis of Natural Products

Course Level: 
Fourth Year
Academic Year: 
2005/2006
Gregory Dake

Office: A341,

604-822-9122
  • mark distribution there will be two midterms and a final examination 
  • weighting (M1/M2/F): 20/30/50; 30/20/50; 15/15/70
  • a passing grade on final guarantees a passing grade in course
  • text: There is no textbook for this course. Feel free to consult your 2nd year organic text; "Advanced Organic Chemistry" Part B by Carey and Sundberg; or "Advanced Organic Chemistry" by March if you want. See me for other options/suggestions.

Course Overview

A. Why and how do organic chemists carry out a total synthesis? What is chemo-, regio-, diastereo- and enantio-selectivity, and why is it important? What is "retrosynthetic analysis" or synthetic planning?

B. Terpene synthesis: seychellene (Piers)

C. Formation of carbon-carbon single bonds

  1. pKa values of organic acids, particularly C-H acids
  2. common bases and solvents, aprotic solvents
  3. alkylation of 1,3-dicarbonyl compounds and related compounds
  4. enolate formation and alkylation
  5. enamine and metalloenamine alkylation processes
  6. conjugate addition reactions
  7. "enantioselective" alkylations

Note: This material is review of 2nd & 3rd year courses and thus will be brieflycovered

D. The aldol reaction: premonensin (Evans)

E. Radical reactions in synthesis: silphiperfolene and capnellene (Curran)

F. Palladium (0) catalysis in synthesis: The Stille, Suzuki and Sonogashira Couplings

G. Formation of carbon-carbon double bonds

  1. thermolysis of sulfoxides and selenoxides
  2. Wittig and Horner-Wadsworth-Emmons reactions
  3. Julia sulfone couplings
  4. Shapiro elimination of sulfonylhydrazones
  5. alkene metathesis

H. Alkaloid synthesis: croomine (Martin)

I. Further topics (if time permits)

Other topics and concepts that will be covered: i) functional group interconversion (oxidation/reduction); ii) protecting groups; iii) conformational analysis; iv) stereoselectivity of reactions; v) chiral auxiliaries

There will be problem sets (no marks except practice) which will be discussed in class.