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Updated: Jan 10, 2026

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Total Synthesis and Absolute Configuration Revision of Biofloranate F.

Shinnosuke Okazaki1, Madoka Oashi1, Koichiro Ota1

  • 1School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.

Chemical & Pharmaceutical Bulletin
|November 19, 2025
PubMed
Summary

Researchers achieved the first total synthesis of biofloranate F, a marine diterpenoid. This study revised the compound's absolute configuration using stereoselective synthesis and an intramolecular Diels-Alder reaction.

Keywords:
absolute configuration revisionbiofloranate Fintramolecular Diels–Alder reactiontotal synthesis

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Area of Science:

  • Organic Chemistry
  • Natural Product Synthesis
  • Marine Natural Products

Background:

  • Biofloranate F is a biflorane-type diterpenoid isolated from the soft coral Lemnalia bournei.
  • Its initial structural assignment required further verification through synthesis.

Purpose of the Study:

  • To achieve the first total synthesis of biofloranate F.
  • To revise the absolute configuration of biofloranate F based on synthetic evidence.

Main Methods:

  • Intramolecular Diels-Alder (IMDA) reaction for constructing the cis-fused decalin core.
  • Evans asymmetric alkylation for establishing stereocenters with high control.
  • Synthesis of both enantiomers to confirm absolute configuration.

Main Results:

  • Successful total synthesis of biofloranate F.
  • Spectroscopic data matched the natural product, but specific rotation was inverted.
  • Synthesis of the enantiomer confirmed the revised absolute configuration: 5S, 6R, 9S, 10R, 11S.

Conclusions:

  • The absolute configuration of biofloranate F was revised to 5S, 6R, 9S, 10R, 11S.
  • The synthetic strategy provides a robust method for accessing related biflorane diterpenoids.