A Novel Oxy‐Oxonia(Azonia)‐Cope Reaction: Serendipitous Discovery and Its Application to the Synthesis of Macrocyclic Musks. Issue 10 (October 2014)

• Record Type: Journal Article
• Authors: Zou, Yue; Zhou, Lijun; Ding, Changming; Wang, Quanrui; Kraft, Philip; Goeke, Andreas
• Is Part Of: Chemistry & biodiversity. Volume 11:Issue 10(2014:Oct.)
• Page Start: 1608
• Page End: 1628
• Publication Date: 2014-10
• Subjects: Biochemistry -- Periodicals; Molecular biology -- Periodicals; Biodiversity -- Periodicals; 572
• DOI: 10.1002/cbdv.201400058
• Languages: English
• ISSNs: 1612-1872

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>This brief review, including new experimental results, is the summary of a talk at the GDCh conference 'flavors &amp; 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‐<italic>Cope</italic> 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 <italic>via</italic> [<italic>n</italic>+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.</p> </abstract>