Synthesis of a Constitutional Isomer of Nerol by Consecutive Ireland–Claisen and Cope Rearrangements

✍ Scribed by Philip Kraft; Walter Eichenberger; Georg Fráter

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 330 KB
• Volume: 1999
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/(sici)1099-0690(199911)1999:11<2781::aid-ejoc2781>3.0.co;2-c

✦ Synopsis

2Z,6E)-3,6-Dimethylocta-2,6-dien-1-ol (6) was synthesized rearrangement of the product at 140°C. A standard LAH reduction in the last step of the synthetic sequence by Steglich esterification of (2E)-2-methylbut-2-en-1-ol (tiglic alcohol, 7) with 3-methylbut-2-en-1-oic acid (senecioic acid, transformed the α,β-unsaturated acid 12 into the target molecule 6, a constitutional isomer of nerol ( ) with 8), followed by selective Ireland-Claisen rearrangement of the resulting ester 9 at 0°C and subsequent Cope interesting olfactory properties.