281. “A Concise Synthesis of Siphonodictidine”
     Jefford, C.W.; Rossier, J.-C.; Boukouvalas, J.; Sledeski, A.W.; Huang, P.-Z.
     J. Nat. Prod. 2004, 67, 1383-1386.

Siphonodictidine (1) has been synthesized for the first time in a concise and regiocontrolled manner by using 2-(tert-butyldimethylsiloxy)-3-methylfuran (6) as the crucial building block. The silver trifluoroacetate-induced alkylation of 6 with ω-bromogeranyl acetate 7 gave the key γ-lactone intermediate 8, which on subsequent reduction, conversion of the hydroxyl into the amino group, and amidination afforded siphonodictidine (1) in an overall yield of 25.7% from 6.

DOI : 10.1021/np0400860 

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