Efficient Macrocyclization by a Novel Oxy-Oxonia-Cope Reaction: Synthesis and Olfactory Properties of New Macrocyclic Musks

• Published in: Chemistry : a European journal Vol. 18; no. 23; pp. 7010 - 7015
• Main Authors: Zou, Yue, Mouhib, Halima, Stahl, Wolfgang, Goeke, Andreas, Wang, Quanrui, Kraft, Philip
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 04-06-2012; WILEY‐VCH Verlag; Wiley Subscription Services, Inc
• Subjects: Alkylation; Chemistry; Correlation; Cyclization; Cycloparaffins - chemical synthesis; Cycloparaffins - chemistry; fragrances; Halogenation; Ketones; macrocycles; Macrocyclic compounds; Macrocyclic Compounds - chemical synthesis; Macrocyclic Compounds - chemistry; Molecular Structure; Musk; Odors; Perfume; Prins reaction; rearrangement; Receptors; Smell; Stereoisomerism; Structure-Activity Relationship; structure-odor relationship; Synthesis; Synthesis (chemistry); Unsaturated
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201200882

Musk made to odor: A new oxy‐oxonia‐Cope macrocyclization to (3Z)‐configured cycloalk‐3‐en‐1‐yl formates is reported, which is useful in the synthesis of unsaturated and saturated macrocyclic ketones (see scheme). The synthesized structures provide new insight into the structure–odor correlation of musks, making it likely for macrocyclic and linear alicyclic musks to address the same olfactory receptors.