title: A novel oxy-oxonia(azonia)-cope reaction: serendipitous discovery and its application to the synthesis of macrocyclic musks.
abstract: 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.
authors.affiliation: Givaudan Fragrances (Shanghai) Ltd., Li Shi Zhen Road 298, Shanghai 201203, P. R. China. barry.zou@givaudan.com.
authors.forename: Yue
authors.initials: Y
authors.lastname: Zou
authors.forename: Lijun
authors.initials: L
authors.lastname: Zhou
authors.forename: Changming
authors.initials: C
authors.lastname: Ding
authors.forename: Quanrui
authors.initials: Q
authors.lastname: Wang
authors.forename: Philip
authors.initials: P
authors.lastname: Kraft
authors.forename: Andreas
authors.initials: A
authors.lastname: Goeke
mesh_terms: D000085:Acetates / Q000737:chemistry*; D004164:Diphosphonates / Q000737:chemistry*; D005229:Fatty Acids, Monounsaturated / Q000737:chemistry*; D006861:Hydrogen Peroxide / Q000737:chemistry*; D047028:Macrocyclic Compounds / Q000138:chemical synthesis*; D015394:Molecular Structure; D010476:Perfume / Q000737:chemistry*
chemical_list: D000085:Acetates; D004164:Diphosphonates; D005229:Fatty Acids, Monounsaturated; D047028:Macrocyclic Compounds; C118890:Oxonia Active; D010476:Perfume; C008563:musk; D006861:Hydrogen Peroxide
keywords: Cope rearrangements; Macrocycles; Ring enlargements; Structureodor relationships