Total Synthesis of the Proposed Structure of Paraphaeosphaeride C.

Kogen Kogen,Kunimura Kunimura,Kobayashi Kobayashi

doi:10.3390/molecules24234230

Kogen Kogen, Kunimura Kunimura + Show 1 more

Open Access

https://doi.org/10.3390/molecules24234230

Copy DOI

Abstract

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.

Highlights

Paraphaeosphaerides A–C (1–3, Figure 1) were isolated from Paraphaeosphaeria neglecta FT462 byCao and co-workers in 2015 [1] and these natural products are structurally related to phaeosphaerides A (4) and B (5) [2]
This paper describes the first total synthesis paraphaeosphaeride paraphaeosphaeride C
This paper describes the first total synthesis proposed structure structure of of paraphaeosphaeride paraphaeosphaeride C

Summary

Introduction

Paraphaeosphaerides A–C (1–3, Figure 1) were isolated from Paraphaeosphaeria neglecta FT462 by. Cao and co-workers in 2015 [1] and these natural products are structurally related to phaeosphaerides. Them,paraphaeosphaeride paraphaeosphaeride C derivative of of phaeosphaeride (4), was wasreported reported to exhibit. 3 mightThus, be a 3 might be a potential lead compound for anti-cancer drug alongside discoveryphaeosphaeride alongside phaeosphaeride. (5),using using a our previous work,we weachieved achievedthe thetotal totalsynthesis synthesis of of phaeosphaerides phaeosphaerides A diastereoselective vinyl anion aldol reaction of aldehyde. 6 to form 7 as the key step a diastereoselective vinyl anion aldol reaction of aldehyde. This paper describes the first total synthesis paraphaeosphaeride paraphaeosphaeride C. 7. This paper describes the first total synthesis proposed structure structure of of paraphaeosphaeride paraphaeosphaeride C

Results and

Unsuccessful

Plausible

Structural

General Experimental Methods

Experimental Procedures and Characterization Data