Presentation is loading. Please wait.

Presentation is loading. Please wait.

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

Published byMuriel Watts Modified over 9 years ago

Similar presentations

Presentation on theme: "Peter Yates ( ) B.Sc from the University of London, 1946."— Presentation transcript:

0 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 , 1981

1 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, Assistant Professor at Harvard, Professor of Chemistry at the University of Toronto, 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.

2 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.

3 Cedranoid Sesquiterpenes

4 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 , The Chemical Society of London (1973)

5 Retrosynthetic Analysis

6 Synthesis

7 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

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

9 Questions?

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

Similar presentations

Formal Total Synthesis of (+/-)-α- and β- Cedrene by Preparation of Cedrone. Construction of the Tricyclic Carbon Skeleton by the Use of a Highly Efficient.

Formal Total Synthesis of (+/-)-α- and β- Cedrene by Preparation of Cedrone. Construction of the Tricyclic Carbon Skeleton by the Use of a Highly Efficient.
Chapter 25 Lipids Jo Blackburn Richland College, Dallas, TX Dallas County Community College District  2006,  Prentice Hall Organic Chemistry, 6 th Edition.

Chapter 25 Lipids Jo Blackburn Richland College, Dallas, TX Dallas County Community College District  2006,  Prentice Hall Organic Chemistry, 6 th Edition.
Synthesis of Vancomycin from the Aglycon Christopher Thompson, Min Ge, Daniel Kahne J. Am. Chem. Soc. 1999, 121, 1237-1244 Presented by James Melnyk.

Synthesis of Vancomycin from the Aglycon Christopher Thompson, Min Ge, Daniel Kahne J. Am. Chem. Soc. 1999, 121, Presented by James Melnyk.
Chemistry Myths and Misunderstandings

Chemistry Myths and Misunderstandings
Natural Products Chemistry Amir E. Wahba, Ph.D. Assistant Professor of Natural Products Chemistry Department Faculty of Science, Damietta University.

Natural Products Chemistry Amir E. Wahba, Ph.D. Assistant Professor of Natural Products Chemistry Department Faculty of Science, Damietta University.
Amos B. Smith Mounuo Cheng 20100911. Prof. Amos B. Smith Rhodes-Thompson Professor of Chemistry University of Pennsylvania, Amos B. Smith, III (born August.

Amos B. Smith Mounuo Cheng Prof. Amos B. Smith Rhodes-Thompson Professor of Chemistry University of Pennsylvania, Amos B. Smith, III (born August.
Condensation and Conjugate Addition Reactions of Carbonyl Compounds

Condensation and Conjugate Addition Reactions of Carbonyl Compounds
Three-component coupling reactions in ionic liquids: a facile synthesis of a-aminonitriles New J. Chem., 2003, 27, 462–465.

Three-component coupling reactions in ionic liquids: a facile synthesis of a-aminonitriles New J. Chem., 2003, 27, 462–465.
INTRODUCTION In the past, a few  -oxygenated  -unsaturated compounds have been selected as substrates for research in the filed of Michael addition.

INTRODUCTION In the past, a few  -oxygenated  -unsaturated compounds have been selected as substrates for research in the filed of Michael addition.
2008 NCNPR TANNIN AWARD Emeritus Professor of Okayama University Professor of Pharmacognosy College of Pharmaceutical Sciences, Matsuyama University Takashi.

2008 NCNPR TANNIN AWARD Emeritus Professor of Okayama University Professor of Pharmacognosy College of Pharmaceutical Sciences, Matsuyama University Takashi.
Last Chem 125 Lecture 4/29/09 Projected material This material is for the exclusive use of Chem 125 students at Yale and may not be copied or distributed.

Last Chem 125 Lecture 4/29/09 Projected material This material is for the exclusive use of Chem 125 students at Yale and may not be copied or distributed.
Organic Synthesis I 1. Main text : Adv. Org. Syn. (4 th Ed.) Part B, Carey & Sundberg 2. Aim : acquiring various reactions and synthetic strategies to.

Organic Synthesis I 1. Main text : Adv. Org. Syn. (4 th Ed.) Part B, Carey & Sundberg 2. Aim : acquiring various reactions and synthetic strategies to.
© 2011 Pearson Education, Inc. 1 Organic Chemistry 6 th Edition Paula Yurkanis Bruice Chapter 27 The Organic Chemistry of Lipids.

© 2011 Pearson Education, Inc. 1 Organic Chemistry 6 th Edition Paula Yurkanis Bruice Chapter 27 The Organic Chemistry of Lipids.
TerpenesTerpenes. Terpenes are a class of molecules that typically contain either ten or fifteen carbon atoms built from a five-carbon building block.

TerpenesTerpenes. Terpenes are a class of molecules that typically contain either ten or fifteen carbon atoms built from a five-carbon building block.
Lecture on the topic: Lipids, their structure and properties. For the 1st year students of specialty “General medicine. Discipline: Chemistry. Lecturer:

Lecture on the topic: Lipids, their structure and properties. For the 1st year students of specialty “General medicine". Discipline: Chemistry. Lecturer:
Photosynthesis. Blank Sheet of Paper Cut the blank sheet of paper in half Cut across the width of the paper Fold each half in half.

Photosynthesis. Blank Sheet of Paper Cut the blank sheet of paper in half Cut across the width of the paper Fold each half in half.
Silas P. Cook Education: B.A. Reed College (1999);

Silas P. Cook Education: B.A. Reed College (1999);
Tetrahydroisoquinoline: Oxidative imine formation, nucleophilic addition reactions and asymmetric selectivity James Fuster, Dr. Rina Soni, Professor Martin.

Tetrahydroisoquinoline: Oxidative imine formation, nucleophilic addition reactions and asymmetric selectivity James Fuster, Dr. Rina Soni, Professor Martin.
The Career of Chao-Jun Li Guochang 2010.7.. B.S. Zhengzhou University 1979 M.S. Chinese Academy of Science 1985 Tak-Hang ChanTak-Hang Chan Ph.D. McGill.

The Career of Chao-Jun Li Guochang B.S. Zhengzhou University 1979 M.S. Chinese Academy of Science 1985 Tak-Hang ChanTak-Hang Chan Ph.D. McGill.
N-Heterocyclic carbenes : A powerful tool in organic synthesis Thomas B UYCK PhD Student in Prof. Zhu Group, LSPN, EPFL Frontiers in Chemical Synthesis.

N-Heterocyclic carbenes : A powerful tool in organic synthesis Thomas B UYCK PhD Student in Prof. Zhu Group, LSPN, EPFL Frontiers in Chemical Synthesis.

Similar presentations

Ads by Google