A cross-metathesis approach to the stereocontrolled synthesis of the AB ring segment of ciguatoxin

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Kadota, Isao; Abe, Takashi; Uni, Miyuki; Takamura, Hiroyoshi; Yamamoto, Yoshinori;
(2008)
  • Journal: Tetrahedron Letters,volume 49,pages3,643-3,647
  • Subject: POLYCYCLIC ETHERS | ABSOLUTE-CONFIGURATION | HYDROXY GROUP | MOIETY | FRAGMENT | SYSTEM | ROUTE | CTX3C

<p>Synthesis of the AB ring segments of ciguatoxin is described. The present synthesis includes a Lewis acid mediated cyclization of allylstannane with aldehyde, cross-metathesis reaction introducing the side chain, and Grieco-Nishizawa dehydration on the A ring.</p>
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