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Expeditious construction of the DEF ring system of thiersinine B
Masaru Enomoto1, Shigefumi Kuwahara
1Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University, Tsutsumidori-Amamiyamachi, Aoba-ku, Sendai 981-8555, Japan.
The Journal of Organic Chemistry
|August 20, 2010
Abstract:
Construction of a DEF ring model of thiersinine B has been achieved from a Wieland-Miescher ketone derivative by a five-step sequence featuring a one-pot regioselective α-allylation of the starting α,β-unsaturated ketone via the Claisen rearrangement and a double dihydroxylation of a dienone intermediate.
