Application of the reaction of D-glucose with meldrum's acid: Total synthesis of the styryl lactones (+)-goniofufurone and (+)-7-epi-goniofufurone

✍ Scribed by Rainer Bruns; Angelika Wernicke; Peter Ko¨ll

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 450 KB
• Volume: 55
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(99)00535-9

✦ Synopsis

The syntheses of the styryl lactones (+)-goniofufurone ( ) and (+)-7-epi-goniofufurone (2) from Dglucose are presented. The key steps are the formation of the lactone moiety by reaction of the hemiace~ais 15 and 16 with meldrum's acid (3) and the addition of phenylmagnesium bromide to the aldehydes 9 or 12. In the last case, we obtained the L-ido and D-gluco configurated products 13 and 14 in a 3:1 mixture. However, addition of ZnCI2 shifted the diastereomeric ratio towards the desired compound 14.