A Concise Synthesis of (−)‐Ambrox

Author:

Wang Bingyang1,Liu Yanhui1,Jia Chenyang1,Lan Zhenfang1,Yang Xuepeng1

Affiliation:

1. Collaborative 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

Abstract

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 %.

Funder

Zhengzhou University of Light Industry

Natural Science Foundation of Henan Province

Publisher

Wiley

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