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Paper | Regular issue | Vol 78, No. 9, 2009, pp.2295-2314
Published online, 19th May, 2009
DOI: 10.3987/COM-09-11720
Trisubstituted Double Bond in the Cyclooctene Ring. Preparation Using the RCM Reaction

Reiko Mizutani, Takuo Miki, Katsuyuki Nakashima, Masakazu Sono, and Motoo Tori*

*Faculty of Pharmaceutical Sciences, Tokushima Bunri University, 180 Nishihamabouji, Yamashiro-machi, Tokushima, 770-8514, Japan


Cyclization to eight-membered rings with a trisubstituted double bond was attempted using ring closing metathesis (RCM) reactions. Although simple substrates were not good candidates, the triene with a proper configuration cyclized to the cyclooctene with a tri-cycle (5-8-6 membered) in moderate yield. The formation of one-carbon smaller rings was also observed.