Peter Yates ( ) B.Sc from the University of London, 1946.

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Peter Yates and K.E. Stevens Bicyclopentanoid Sesquiterpenes. The Synthesis of Cedranoid Sesquiterpenes via the Photo-Rearrangement of Bicyclo[2.2.2]Octenones Peter Yates and K.E. Stevens Tetrahedron Vol.37, No. 25, pp.4401-4410, 1981

Peter Yates (1924-1992) B.Sc from the University of London, 1946. Ph.D with Werner Bergmann from Yale, 1951. Postdoctoral fellow with R. B. Woodward at Harvard, 1950-1951. Assistant Professor at Harvard, 1952-1960 Professor of Chemistry at the University of Toronto, 1960-1992 Published over 200 papers. Caspase recruitment domains (CARDs) Nucleotide-binding oligomerization (NOD) domain Leucine-rich repeat (LRR). Peter Yates is well know for his structural characterization of Mangosteen, Shellolic Acid, and Haplophytine and the synthesis of Gambogic acid and Cedrene.

Cedranoid Sesquiterpenes Sesquiterpenes are a class of terpenes that are made up of three 5 carbon isoprene units. These molecules are found in plants and insects. Can act as defensive agents or pheromones. Very diverse in structure. C15H24 Farnesyl pyrrophosphate (FPP) is the precursor to most sesquiterpenes.

Cedranoid Sesquiterpenes

Past Syntheses of Cedranoids None of these routes allow for more highly oxygenated cedranoids. 1.G. Stork and F.H. Clarke Jr., J. Am. Chem. Soc. 77, 1072 (1955); 83, 3114 (1961). 2. W. Parker, J.S. Roberts and R. Ramage, Quart. Rev. (London). 21, 331 (1967); J. S. Roberts, Terpenoids and Steroids (Edited by K. H. Overton), Vol. III, pp. 121-123, The Chemical Society of London (1973)

Retrosynthetic Analysis

Synthesis

Oxa-di-π-methane Rearrangement This reaction takes place solely from the triplet state. (π-π*) Direct irradiation of β, γ unsaturated ketones gives rise to processes other than the oxa-di-π-methane rearrangement. (Suggests inefficient intersystem crossing) Acetophenone is used as a triplet sensitizer. Three Possible Mechanisms for Action

Conclusion Synthesis of β-diketone Intermediate in the synthesis of Stork and Clarke. Should allow for addition oxygenated functions along the carbon backbone.

Questions?