Expeditious construction of the DEF ring system of thiersinine B.
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.
Enomoto
Masaru
M
Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University, Tsutsumidori-Amamiyamachi, Aoba-ku, Sendai 981-8555, Japan.
Kuwahara
Shigefumi
S
D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D004224:Diterpenes; D007211:Indoles; D007659:Ketones; C471500:thiersinine B