Synthesis of fulgidic acid and the two possible stereoisomers of chaenomic acid D

文献情報

出版日 2023-12-19

DOI 10.1039/D3OB01820B

インパクトファクター 3.876

著者

Narihito Ogawa, Keisuke Gonda, Yuichi Kobayashi

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要旨

We synthesized fulgidic acid and the proposed structure for chaenomic acid D. The core part of the two natural products was constructed stereoselectively by the addition of acetic acid to the α,β-unsaturated epoxy alcohol in the presence of a palladium catalyst. Subsequently, the two natural products were synthesized from the intermediate in a few steps. The data for the synthesized fulgidic acid were in good agreement with the reported data. Chaenomic acid was in good agreement with the natural product in the 1H and 13C NMR data, but not in the optical rotation. The 15R-isomer of chaenomic acid was also synthesized, but the 1H and 13C NMR data did not agree with the natural product.

掲載誌

Organic & Biomolecular Chemistry

CiteScore: 3.4

自己引用率: 10.3%

年間論文数: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Synthesis of fulgidic acid and the two possible stereoisomers of chaenomic acid D

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