Author/Authors :
Fujiwara، نويسنده , , Kenshu and Aki، نويسنده , , Yuichi and Yamamoto، نويسنده , , Fuyuki and Kawamura، نويسنده , , Mariko and Kobayashi، نويسنده , , Masanori and Okano، نويسنده , , Azusa and Awakura، نويسنده , , Daisuke and Shiga، نويسنده , , Shunsuke and Murai، نويسنده , , Akio and Kawai، نويسنده , , Hidetoshi and Suzuki، نويسنده , , Takanori، نويسنده ,
Abstract :
In this study, we synthesized the C8–C20 and C21–C30 segments of the diarrhetic shellfish toxin pectenotoxin 2. The C8–C20 segment was assembled from a phosphonate corresponding to the C8–C15 segment (prepared from l-malic acid in 19 steps) and an aldehyde corresponding to the C16–C20 segment (synthesized from 3-methyl-3-butenol in nine steps) by a twelve-step process including the Horner–Wadsworth–Emmons reaction, regio- and stereoselective reduction of the resulting enone, diastereoselective epoxidation, and 5-exo epoxide cleavage forming the C-ring. The C21–C30 segment was constructed in 13 steps from (S)-glycidol via a route involving E-ring formation by 5-exo epoxide cleavage and stereoselective methylation at C27 by the Evans method.
