A Concise Synthesis of (-)-Ambrox.

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

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Article in ChemistryOpen, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

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1citing papers in PubMed

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1 citing paper in PubMed.

A Concise Synthesis of (-)-Ambrox.ChemistryOpen · 2024
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5 · Who and what money

Authors and funding

5 authors.

Bingyang WangCollaborative Innovation Center for Food Production and Safety, Zhengzhou University of Light Industry, Zhengzhou University of Light Industry, Dongfeng Road 5, Zhengzhou, Henan, 450002, People's Republic of China.

Yanhui LiuCollaborative Innovation Center for Food Production and Safety, Zhengzhou University of Light Industry, Zhengzhou University of Light Industry, Dongfeng Road 5, Zhengzhou, Henan, 450002, People's Republic of China.

Chenyang JiaCollaborative Innovation Center for Food Production and Safety, Zhengzhou University of Light Industry, Zhengzhou University of Light Industry, Dongfeng Road 5, Zhengzhou, Henan, 450002, People's Republic of China.

Zhenfang LanCollaborative Innovation Center for Food Production and Safety, Zhengzhou University of Light Industry, Zhengzhou University of Light Industry, Dongfeng Road 5, Zhengzhou, Henan, 450002, People's Republic of China.

Xuepeng YangCollaborative Innovation Center for Food Production and Safety, Zhengzhou University of Light Industry, Zhengzhou University of Light Industry, Dongfeng Road 5, Zhengzhou, Henan, 450002, People's Republic of China.

Funding

Natural Science Foundation of Henan Province 232300420383Zhengzhou University of Light Industry 2021BSJJ004

6 · The paper itself

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 %.

Indexed as

(−)-ambrox(R)-carvonesynthesis

Identifiers

PMID38775626

DOI10.1002/open.202400006

PMCPMC11467728

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.