A concise synthesis of siphonodictidine.
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.
Jefford
Charles W
CW
Department of Organic Chemistry, University of Geneva, 30 quai Ernest-Ansermet, 1211 Geneva 4, Switzerland. Charles.Jefford@chiorg.unige.ch
Rossier
Jean-Claude
JC
Boukouvalas
John
J
Sledeski
Adam W
AW
Huang
Ping-Zhong
PZ
D000478:Alkylation; D000818:Animals; D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000737:chemistry; D011161:Porifera / Q000737:chemistry; D012717:Sesquiterpenes / Q000032:analysis / Q000138:chemical synthesis*; D013237:Stereoisomerism
C492415:2-(tert-butyldimethylsiloxy)-3-methylfuran; D005663:Furans; D007202:Indicators and Reagents; D017646:Organosilicon Compounds; D012717:Sesquiterpenes; C492414:siphonodictidine