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A Concise Synthesis of Siphonodictidine

Rossier, Jean-Claude
Boukouvalas, John
Sledeski, Adam W.
Huang, Ping-Zhong
Published in Journal of Natural Products. 2004, vol. 67, no. 8, p. 1383-1386
Abstract 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 omega-bromogeranyl acetate 7 gave the key gamma-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.
PMID: 15332858
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JEFFORD, Charles et al. A Concise Synthesis of Siphonodictidine. In: Journal of Natural Products, 2004, vol. 67, n° 8, p. 1383-1386. doi: 10.1021/np0400860 https://archive-ouverte.unige.ch/unige:7927

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Deposited on : 2010-06-21

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