A highly efficient route was developed to synthesize (-)-8-epigrosheimin in four steps from aldehyde 2 based on a substrate-controlled method. The key steps of the synthesis included (1) a stereo- and regioselective allylation addition, (2) an intramolecular translactonization, and (3) an aldehyde-ene cyclization.
Synthesis and in vitro antitumor activity of new butenolide-containing dithiocarbamates
Three series of butenolide-containing dithiocarbamates were designed and synthesized. Their anti-tumor activity in vitro was evaluated. Among them compound I-14 exhibited broad spectrum anti-cancer activity against five human cancer cell lines with IC50 30 μM. Structure-activity relationship analysis showed that the introduction of dithiocarbamate side chains on the C-3 position of butenolide was crucial for anti-tumor activity.
Syntheis of 3-(1-Hydroxyalkyl)-5H-furan-2-ones: Study of their Reaction with Halogens
The syntheis of 3-(1-hydroxyalkyl)-5H-furan-2-ones, 4a-c, is reported.The reaction of lactones 4a and 4b with bromine under typical ionic bromination conditions gives as major product the unexpected substitution of the allylic hydroxyl group.Only the less hindered double bond in 4c gives some proportion of the normal addition product.The bromine chloride addition to 4c proceeds with 55 percent yield, while lactone 4a does not add BrCl.All these results point to the fact that halogen addition to the double bond of 4 suffers at least from steric hindrance.Key words: 3-(1-hydroxyalkyl)-5H-furna-2-ones; bromination; bromine chlorination
Calderon, Angel,March, Pedro de,Arrad, Mustafa el,Font, Josep
p. 4201 - 4214
(2007/10/02)
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