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

IF 3.6 2区生物学 Q2 CHEMISTRY, MEDICINAL

Journal of Natural Products Pub Date : 2025-08-26 DOI:10.1021/acs.jnatprod.5c00838

Yuta Inori, , , Hirosato Takikawa, , and , Yusuke Ogura*,

引用次数: 0

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.

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沉香中一种重要芳香化合物(+)-卡拉酮的不对称全合成。

摘要首次以4-戊烯-2-醇为原料，经17步合成了高档沉香木（Kyara）中的关键香气化合物(+)-卡拉酮。C7、C4和C5的关键立体中心通过不对称醛缩和Ireland-Claisen重排得到。C8上的氧官能团是通过氧化重排形成的，(+)-卡拉酮的双环核是通过合环复分解形成的。还合成了两个相关化合物(+)-4-外延卡拉酮和(+)-华氏二酮。对(+)-卡拉酮、(+)-4-外延卡拉酮和(+)-华氏二酮的结构-气味关系进行了研究。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Journal of Natural Products 生物-药学

CiteScore

9.10

自引率

5.90%

发文量

294

审稿时长

2.3 months

期刊介绍： The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin. When new compounds are reported, manuscripts describing their biological activity are much preferred. Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.