Total Synthesis of the Proposed Structure of Paraphaeosphaeride C

• Main Authors: Kenichi Kobayashi, Risako Kunimura, Hiroshi Kogen
• Format: Article
• Language: English
• Published: MDPI AG 2019-11-01
• Series: Molecules
• Subjects: paraphaeosphaeride c; stat3; anti-cancer; total synthesis; stereoselective synthesis
• Online Access: https://www.mdpi.com/1420-3049/24/23/4230
• ISSN: 1420-3049

Paraphaeosphaeride C is a demethoxy derivative of phaeosphaeride A and exhibits STAT3 inhibitory activity. Our previous papers reported the total synthesis of phaeosphaeride A using a diastereoselective vinyl anion aldol reaction as the key step to construct the dihydropyran ring. In this work, the first total synthesis of the proposed structure of paraphaeosphaeride C was achieved via a similar synthetic strategy. The synthetic compound was characterized through extensive nuclear magnetic resonance (NMR) analysis but the ¹H and ¹³C-NMR data for this compound did not correspond to those reported in the literature for paraphaeosphaeride C.