The synthesis of 10,11-dimethyl-eicosan-1,20-dioic acid

✍ Scribed by Roger A. Klein

• Book ID: 103036965
• Publisher: Elsevier Science
• Year: 1980
• Tongue: English
• Weight: 533 KB
• Volume: 26
• Category: Article
• ISSN: 0009-3084
• DOI: 10.1016/0009-3084(80)90005-5

✦ Synopsis

10,11-Dimethyl-elcosan-l,20-dlotc acid has been syntheslsed from undec-10-enolc acid via the TMS ether of either the 10-bromo or 10-1odo-alcohol Crude yields from the 10-bromo-alcohol for the Wurtz reaction were 31% directly and 44% wa the 10-1odo-compound Overall yields of the dtmethyl ester of 10,1 l-dtmethyl-emosan-l,20-dlolc acid from the TMS ether of 10-bromoundecan-l-ol, used as starting materml in both cases were 15% and 31% respectively Both the rneso-compound and the racermc mixture were produced by this reaction In conJunction with the data obtained from biologically synthestsed material it is possible to assign the NMR signals assocmted with both meso and racemzc forms