Ring-closing alkyne metathesis.: Application to the total synthesis of sophorolipid lactone

被引:113
作者
Fürstner, A [1 ]
Radkowski, K [1 ]
Grabowski, J [1 ]
Wirtz, C [1 ]
Mynott, R [1 ]
机构
[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
关键词
D O I
10.1021/jo0012952
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first total synthesis of a major component of the microbial biosurfactant sophorolipid has been achieved. This approach-to the 26-membered macrolide 1 containing a Z-configured alkene group in its lipidic tether spanning the sophorose backbone is based on a ring-closing metathesis reaction of diyne 21 catalyzed by Mo[N(t-Bu)(Ar)](3) (5; Ar = 3,5-dimethylphenyl) activated in situ by CH2-Cl-2, followed by Lindlar reduction of the resulting cycloalkyne 22. The two beta -glycosidic linkages of compound 21 were installed by means of the glucal epoxide method and a modified Koenigs-Knorr reaction promoted by AgOTf/lutidine, respectively.
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页码:8758 / 8762
页数:5
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