Synthesis of trans-fused tetrahydrooxepins: stereoselective allylation of sulfur or fluoro-substituted tetrahydrooxepins.
An efficient route to the trans-fused tetrahydrooxepin corresponding to the E ring of ciguatoxin was developed. Wide screening of allylation reactions of sulfur or fluoro-substituted tetrahydrooxepin revealed that the optimum method for obtaining the beta-allylation product selectively was the use of a combination of allyltrimethylsilane and TiCl(4) with 6-fluoro-7-hydroxytetrahydrooxepin.
Kobayashi
Shoji
S
Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai 599-8531, Japan. koba@c.s.osakafu-u.ac.jp
Hori
Makiko
M
Hirama
Masahiro
M
D000475:Alkenes; D002922:Ciguatoxins / Q000737:chemistry; D005461:Fluorine; D010082:Oxepins / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013455:Sulfur; D014297:Trimethylsilyl Compounds
D000475:Alkenes; D010082:Oxepins; D014297:Trimethylsilyl Compounds; D002922:Ciguatoxins; D005461:Fluorine; D013455:Sulfur; C440774:allyltrimethylsilane