Convenient Syntheses and Biological Activity of Novel ω-trans-(Bicyclopropyl)- and ω-(Bicyclopropylidenyl)-Substituted Fatty Acids and Their Derivatives
✍ Scribed by Sandra Löhr; Carsten Jacobi; Andre Johann; Gerhard Gottschalk; Armin de Meijere
- Publisher
- John Wiley and Sons
- Year
- 2000
- Tongue
- English
- Weight
- 261 KB
- Volume
- 2000
- Category
- Article
- ISSN
- 1434-193X
No coin nor oath required. For personal study only.
✦ Synopsis
A series of ω-trans-(bicyclopropyl)-substituted fatty acids 9 has been synthesized from bicyclopropylidene (5) starting by deprotonation with n-butyllithium. Electrophilic substitution of lithiobicyclopropylidene with THP-protected ω-iodoalkanols 6 gave the THP-protected (bicyclopropylidenyl)alkanols 7 in 63-88% yield. A reasonably diastereoselective reduction of the bicyclopropylidene moiety in 7 was achieved with lithium in liquid ammonia, and deprotection of the resulting trans-(bicyclopropyl)alkanol derivatives 8 followed by Jones oxidation provided the fatty acids 9 in yields ranging from 59 to 75%. ω-Bicyclopropylidenyl-substituted fatty acids 11 were prepared by deprotection and oxidation of the THP-