Total Synthesis of Bioactive Natural Products by Palladium-Catalyzed Domino Cyclization of Allenes and Related Compounds

1. Front Matter

   Pages i-xvi

   PDF

2. Introduction

   • Shinsuke Inuki

   Pages 1-8

3. Total Synthesis of Pachastrissamine (Jaspine B)

   1. Front Matter

      Pages 9-9

      PDF

   2. Total Synthesis through Palladium-Catalyzed Bis-Cyclization of Bromoallenes

      • Shinsuke Inuki

      Pages 11-27

   3. Total Synthesis through Palladium-Catalyzed Bis-Cyclization of Propargyl Chlorides and Carbonates

      • Shinsuke Inuki

      Pages 29-49

4. Total Synthesis of Lysergic Acid, Lysergol, and Isolysergol

   1. Front Matter

      Pages 51-51

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   2. Palladium-Catalyzed Domino Cyclization of Amino Allenes Bearing a Bromoindolyl Group and Its Application to Total Synthesis of Ergot Alkaloids

      • Shinsuke Inuki

      Pages 53-75

   3. Total Synthesis of (+)-Lysergic Acid, (+)-Lysergol, and (+)-Isolysergol

      • Shinsuke Inuki

      Pages 77-103

   4. Conclusions

      • Shinsuke Inuki

      Pages 105-106

The author has developed novel methodologies for highly efficient construction of functionalized heterocycles by palladium-catalyzed domino/cascade cyclization of allenes and related compounds containing appropriate nucleophilic group(s). Based on these methodologies, enantioselective total syntheses of bioactive natural products, pachastrissamine (26% overall yield in seven steps), lysergic acid (4.0% overall yield in fifteen steps), lysergol (3.6% overall yield in fifteen steps) and isolysergol (8.2% overall yield in eleven steps) have been achieved. These are more facile synthetic route than those previously reported. These findings would contribute to the development of efficient synthetic methods for biologically active compounds containing a complex structure.

• allene cyclization
• bioactive natural products
• ergot alkaloid
• functionalized heterocycles
• naural products
• palladium-catalyzed cascade cyclization
• palladium-catalyzed domino cyclization
• total synthesis

From the reviews:

“The target audience … includes practicing organic chemists with interests in synthesis, and those with specific interests in palladium-catalysed organic reactions, and as such is suited to graduate level and above. … is well-written and provides plenty of food for thought for specialists in palladium(II) chemistry … . the book also benefits from a comprehensive experimental section at the end of each chapter. … the book reflects the high quality experimental skills of the author, and provides a useful handbook for the synthetic organometallic chemist.” (Edward A. Anderson, Platinum Metals Review, Vol. 56 (3), 2012)

• FUJIFILM Corporation, Kanagawa, Japan

  Shinsuke Inuki

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