Convergent synthesis of pyragonicin
Shunya Takahashi1, Yayoi Hongo, Narihito Ogawa
1RIKEN (The Institute of Physical and Chemical Research), Wako-shi, Saitama, 351-0198, Japan. shunyat@riken.go.jp
Abstract:
This paper describes a second-generation synthesis of an antitumor tetrahydropyran (THP) acetogenin, pyragonicin. The key step involved an olefin cross-metathesis between the THP segment and the terminal gamma-lactone residue. The coupling reaction in the presence of Grubbs' second-generation catalyst resulted in an unseparable mixture of a desired coupling product and its one-carbon eliminated product while the use of Grubbs' first-generation catalyst afforded the former exclusively. A novel MOM-migrating reaction found in a cyclization reaction is also discussed.
More Related Videos
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
14:11Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Related Concept Videos
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Biosynthesis in Bacteria
Peptidoglycan Synthesis
Biosynthesis of Nucleic Acids
Production of Antibiotics
Production of Pharmaceuticals
