Synlett p. 1227 - 1230 (1999)
Update date:2022-08-11
Topics:
Siegel, Konrad
Brückner, Reinhard
Starting from L-ascorbic acid, crotonaldehyde, (trimethylsilyl)acetylene and the stannylated alcohol 15, the title compound 4 was synthesized for the first time. L-Ascorbic acid was elaborated into phosphonium bromide 19 with a high degree of Z-stereoselectivity while the other starting materials were combined for obtaining the unsaturated aldehyde 5. A Wittig reaction between this aldehyde and the ylide derived from bromide 19 provided xerulin (4) along with a mixture of isomers which was readily separable.
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