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Bioinspired Total Synthesis and Structural Reidentification of Alstrostines.

Daiki Hiruma1, Akiho Yoshidome1,2, Kenta Rakumitsu1

  • 1Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba, 260-8675, Japan.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|February 18, 2025
PubMed
Summary

Researchers achieved the first asymmetric total syntheses of complex monoterpenoid indole alkaloids, alstrostine A and isoalstrostine A. This breakthrough clarifies their structures and revises alstrostine A

Keywords:
Bioinspired reactionCollective synthesisIridoid glycosideMonoterpenoid indole alkaloidTotal synthesis

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Area of Science:

  • Natural Product Chemistry
  • Synthetic Organic Chemistry
  • Medicinal Chemistry

Background:

  • Alstrostine A and isoalstrostine A are complex monoterpenoid indole alkaloid glycosides from Apocynaceae and Rubiaceae plants.
  • Their large size, multiple chiral centers, and fused structures make structural elucidation via spectral analysis extremely challenging.
  • Total synthesis is crucial for definitive structural identification and understanding these natural products.

Purpose of the Study:

  • To achieve the first asymmetric total syntheses of alstrostine A and isoalstrostine A.
  • To confirm and revise the proposed stereochemistry of alstrostine A.
  • To develop a synthetic strategy applicable to related complex alkaloids.

Main Methods:

  • Development of an 18- or 19-step asymmetric total synthesis.
  • Utilized a key two- or three-component coupling reaction between secologanin and a pyrrolidinoindoline moiety.
  • Synthesized all isomers of the pyrrolidinoindoline fragment to explore stereochemical possibilities.

Main Results:

  • Successful completion of the first asymmetric total syntheses of alstrostine A and isoalstrostine A.
  • The synthetic approach allowed for the revision of the stereochemistry of alstrostine A.
  • A previously identified compound was re-identified as epialstrostine A, a new stereoisomer.

Conclusions:

  • The total synthesis provides unambiguous structural confirmation of alstrostine A and isoalstrostine A.
  • The study revises the stereochemistry of alstrostine A and introduces epialstrostine A.
  • The developed synthetic strategy is valuable for accessing complex indole alkaloid glycosides.