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Expeditious tandem-metathesis route to the AB-ring fragment of ciguatoxin

✍ Scribed by Hiroki Oguri; Shin-ya Sasaki; Tohru Oishi; Masahiro Hirama


Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
231 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis


The AB-ring fragment of ciguatoxin was synthesized in ten steps from tri-O-benzyl-D-glucal based on a highly diastereoselective ring-closing metathesis and subsequent cross metathesis.


πŸ“œ SIMILAR VOLUMES


A cross-metathesis approach to the stere
✍ Isao Kadota; Takashi Abe; Miyuki Uni; Hiroyoshi Takamura; Yoshinori Yamamoto πŸ“‚ Article πŸ“… 2008 πŸ› Elsevier Science 🌐 French βš– 129 KB

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.