Zou Yue, Zhou Lijun, Ding Changming, Wang Quanrui, Kraft Philip, Goeke Andreas
Givaudan Fragrances (Shanghai) Ltd., Li Shi Zhen Road 298, Shanghai 201203, P. R. China.
Chem Biodivers. 2014 Oct;11(10):1608-28. doi: 10.1002/cbdv.201400058.
This brief review, including new experimental results, is the summary of a talk at the GDCh conference 'flavors & fragrances 2013' in Leipzig, Germany, 11th-13th September, 2013. Musk odorants are indispensable in perfumery to lend sensuality to fine fragrances, a nourishing effect to cosmetics, and a comforting feeling to laundry. We have recently found serendipitously a new oxy-oxonia-Cope rearrangement. In this account, we review the background of oxonia-sigmatropic rearrangements and the discovery of this novel reaction. Special attention is focused on the versatile lactone and lactam formation reactions via [n+4] ring enlargement and the macrocyclization in the synthesis of new macrocyclic musks. The synthesized structures provide new insights into the structure-odor relationships of musks.
本简要综述，包括新的实验结果，是2013年9月11日至13日在德国莱比锡举行的德国化学会“香料与香精2013”会议上一场报告的总结。麝香类香料在香水制造业中不可或缺，能为优质香水增添性感魅力，为化妆品带来滋养效果，为洗涤用品营造舒适感受。我们最近偶然发现了一种新的氧-氧鎓-科普重排反应。在此报告中，我们回顾了氧鎓-σ迁移重排反应的背景以及这一新型反应的发现过程。特别关注了通过[n+4]扩环形成内酯和内酰胺的多功能反应以及新大环麝香合成中的大环化反应。所合成的结构为麝香的结构与气味关系提供了新的见解。
