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Paper | Regular issue | Vol 71, No. 3, 2007, pp.627-634
Published online, 30th January, 2007
DOI: 10.3987/COM-06-10972
Total Synthesis of (S)-(+)- and (R)-(-)-Curcudiols Based on 1,2-Aryl Migration via Phenonium Ion

Takeru Ehara, Hirofumi Yokoyama, Machiko Ono, and Hiroyuki Akita*

*School of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, Japan


Total synthesis of (S)-(+)- and (R)-(-)-curcudiols (2) was achieved based on the 1,2-aryl migration of the (4R,5R)- and (4S,5S)-4-aryl-5-tosyloxy-(2E)-hexenoates (9) derived from (4R,5R)- and (4S,5S)-4-epoxy-(2E)-hexenoates (3), respectively.