Author/Authors :
Takizawa، نويسنده , , Ayumi and Fujiwara، نويسنده , , Kenshu and Doi، نويسنده , , Eriko and Murai، نويسنده , , Akio and Kawai، نويسنده , , Hidetoshi and Suzuki، نويسنده , , Takanori، نويسنده ,
Abstract :
The common FGHI-ring part (2) of ciguatoxins has been synthesized from the F- and I-ring parts (6 and 5, respectively). The Nozaki–Hiyama–Kishi coupling of 6 with 5 followed by regio- and stereoselective epoxidation at C29 and C30 afforded an epoxide (4), which was transformed into a tricyclic compound (3) corresponding to the F-HI-ring part by 6-exo-epoxide opening and the subsequent inversion of the C29 stereocenter. Reductive cyclization of 3 forming the C31–O26 bond of the G-ring successfully produced 2.
Keywords :
Convergent synthesis , trans-Fused polycyclic ether , ciguatoxin , natural product synthesis
