A Concise Synthesis of (−)-Ambrox

IF 2.5 4区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

ChemistryOpen Pub Date : 2024-05-22 DOI:10.1002/open.202400006

Bingyang Wang, Yanhui Liu, Chenyang Jia, Zhenfang Lan, Xuepeng Yang

引用次数: 0

Abstract

(−)-Ambrox, a highly prized and commercially significant component of ambergris, finds widespread application in perfumery, cigarettes, cosmetics, and the food industry. Despite considerable attention to this research area over the years, an environmentally friendly and practical method for synthesizing (−)-ambrox has remained elusive. This study presents a succinct and efficient approach to (−)-ambrox synthesis, involving two consecutive alkylations at C-6, followed by an acid-catalyzed cyclization to give bicyclic ketones starting from (R)-carvone. Subsequent reduction, Barton Vinyl Iodide synthesis, alkylation, and an acid-catalyzed cyclization collectively achieved the synthesis of (−)-ambrox with a satisfactory yield of 26.2 %.

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(-)-Ambrox 的简明合成。

(-)-Ambrox 是龙涎香中一种非常珍贵且具有重要商业价值的成分，广泛应用于香水、香烟、化妆品和食品工业。尽管多年来人们对这一研究领域给予了极大的关注，但一种环保实用的 (-)-Ambrox 合成方法仍未问世。本研究提出了一种简洁高效的 (-)-ambrox 合成方法，包括在 C-6 处连续进行两次烷基化，然后在酸催化下进行环化，以 (R)-carvone 为起点生成双环酮。随后的还原、巴顿碘化乙烯合成、烷基化和酸催化环化共同完成了 (-)-ambrox 的合成，收率达到 26.2%，令人满意。

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

ChemistryOpen CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

4.80

自引率

4.30%

发文量

143

审稿时长

1 months

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