The Asymmetric Total Synthesis and Configuration Confirmation of Aplysiaenal and Nhatrangin A, Truncated Derivatives of Aplysiatoxin and Oscillatoxin

J Nat Prod. 2023 Apr 28;86(4):1033-1041. doi: 10.1021/acs.jnatprod.3c00077. Epub 2023 Mar 31.

Abstract

Asymmetric total syntheses of aplysiaenal (1) and nhatrangin A (2), truncated derivatives of the aplysiatoxin/oscillatoxin family of marine natural products, from configurationally defined intermediates are described. NMR spectra of our synthesized nhatrangin A did not match with either those obtained from authentic samples of the natural product or material obtained via two other total syntheses, but were similar to that obtained from a sample obtained in a third total synthesis. By independently synthesizing the fragments used in its total syntheses, we were able to confirm the configuration of nhatrangin A and clarified that the discrepancy in the spectroscopic data is due to salt formation of the carboxylic acid moiety.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Lyngbya Toxins* / chemistry
  • Magnetic Resonance Spectroscopy
  • Stereoisomerism

Substances

  • nhatrangin A
  • aplysiatoxin
  • Lyngbya Toxins