Asymmetric Total Synthesis of (+)-Karanone: An Important Aroma Compound in Fine Agarwood.

Authors

Yuta Inori, Hirosato Takikawa, Yusuke Ogura

Published in

Journal of natural products. Aug 26, 2025. Epub Aug 26, 2025.

Abstract

The first asymmetric total synthesis of (+)-karanone, a key aroma compound in high-grade agarwood ("Kyara"), was accomplished in 17 steps from 4-penten-2-ol. The key stereocenters at C7, C4, and C5 were introduced via asymmetric aldol condensation and Ireland-Claisen rearrangement. The oxygen-functional group at C8 was formed through oxidative rearrangement, and the bicyclic core of (+)-karanone was constructed by ring-closing metathesis. Two related compounds, namely (+)-4-epi-karanone and (+)-warburgiadione, were also synthesized. Studies of the structure-odor relationship among (+)-karanone, (+)-4-epi-karanone, and (+)-warburgiadione were also performed.

PMID:
40857669
Bibliographic data and abstract were imported from PubMed on 27 Aug 2025.

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