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SINTESIS

SINTESIS. Prostaglandines (PGs) Taxol Palytoxin. Total Synthesis of Prostaglandines (PGs). Strategy and method. Department of Chemistry, Graduate School of Science, Kobe University Masahiko Hayashi. Total Synthesis of Prostaglandins (PGs). Corey: 1990 Nobel Prize: linear synthesis

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SINTESIS

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  1. SINTESIS • Prostaglandines (PGs) • Taxol • Palytoxin

  2. Total Synthesis of Prostaglandines (PGs) Strategy and method Department of Chemistry, Graduate School of Science, Kobe UniversityMasahiko Hayashi

  3. Total Synthesis of Prostaglandins (PGs) Corey: 1990 Nobel Prize: linear synthesis Noyori: 2001 Nobel Prize: convergent synthesis Corey’s method vs Noyori’s method

  4. Significance of the synthesis of Prostaglandins (PGs) It is necessary to synthesize PGs, because the quantity in nature (in animals including human being) is too little for actual medical treatment. Artificial modification is possible by synthesis. For example, the analogues of Prostacyclins (PGI2). Natural PGI2 is very unstable as a drug.

  5. bioactive = drug

  6. C O H C O H 2 2 R O R O O R O R Retrosynthetic analysis O O convergent linear Noyori’s method Corey’s method

  7. convergent synthesis linear synthesis

  8. ( C H ) P 6 5 3 - + C O M 2 C O H C H O 2 R O R O O R O R C H O R O R O O R Retrosynthetic Analysis of Corey’s Method O O Wittig O O O O Wittig

  9. Do not confuse relative configuration and absolute configuration! So far, control of relative configuration (racemic compound) was done, so optical resolution is necessary to obtain chiral compound!

  10. stable ylide = unreactive unstable ylide = reactive

  11. conversent synthesis linear synthesis

  12. Noyori’ s method

  13. Three component coupling

  14. Michael addition + Enolate trap

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