A Novel Oxy-Oxonia(Azonia)-Cope Reaction: Serendipitous Discovery and Its Application to the Synthesis of Macrocyclic Musks

作者：Zou Yue^*; Zhou Lijun; Ding Changming; Wang Quanrui; Kraft Philip; Goeke Andreas

来源：Chemistry and Biodiversity, 2014, 11(10): 1608-1628.

DOI：10.1002/cbdv.201400058

• Cope rearrangements
• Ring enlargements
• Macrocycles
• Structureodor relationships

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 structureodor relationships of musks.

• 出版日期2014-10
• 单位复旦大学