Related Experiment Video
Updated: Aug 17, 2026

From a Natural Product to Its Biosynthetic Gene Cluster: A Demonstration Using Polyketomycin from Streptomyces diastatochromogenes Tü6028
Published on: January 13, 2017
Total synthesis of the proposed structure for pyragonicin
Shunya Takahashi1, Narihito Ogawa, Hiroyuki Koshino
1RIKEN (The Institute of Physical and Chemical Research), Wako, Saitama 351-0198, Japan. shunyat@postman.riken.go.jp
Abstract:
[structure: see text] The total synthesis of acetogenin 1 reported for pyragonicin and its 10-epimer 32 is described. The common THP ring system was stereoselectively constructed through a SmI(2)-induced reductive cyclization of beta-alkoxy acrylate 5 followed by Mitsunobu inversion, and each chiral center at C-10 was created by Brown's asymmetric allylation. Compound 1 had spectroscopic data consistent with that of natural pyragonicin, but a different optical rotation.
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
11:44Synthesis and Structure Determination of µ-Conotoxin PIIIA Isomers with Different Disulfide Connectivities
Published on: October 2, 2018
Related Concept Videos
Peptidoglycan Synthesis
Production of Antibiotics
Biosynthesis of Nucleic Acids