- Ruthenium-Catalyzed Cross-Metathesis of Allyl Acetate and Styrenes: A Practical Approach to the Synthesis of Tripolinolate A and Its Analogs
-
The scope of the Ru-catalyzed cross-metathesis of allyl acetates and styrenes was explored. A variety of electronically and structurally divergent styrenes were tolerated, and the resultant products were obtained in reasonable yields. The reported method was utilized in the synthesis of inhibitors of the proliferation of glioma and colorectal cancer cells, tripolinolate A and its diacetate analog.
- Araki, Yasuhiro,Topolov?an, Nikola,Kotora, Martin
-
supporting information
p. 1736 - 1739
(2017/04/13)
-
- Part 148 in the series "studies on novel synthetic methodologies:" Selective acetylation of alcohols, phenols and amines and selective deprotection of aromatic acetates using silica-supported phosphomolybdic acid
-
An environmentally friendly silica-supported phosphomolybdic acid was found to be a highly efficient catalyst for the selective acetylation of alcohols, phenols and amines in the absence of any solvent and also for the chemoselective deprotection of aromatic acetates under very mild conditions. This method has been used for the protection of the hydroxy groups as well as for the deprotection of the acetates of several naturally occurring bioactive phenolic compounds. The catalyst can be easily recovered and reused.
- Das, Biswanath,Thirupathi, Ponnaboina,Kumar, Rathod Aravind,Laxminarayana, Keetha
-
p. 2677 - 2683
(2008/09/19)
-
- Synthesis and Reactivity of Vinyl Quinone Methides
-
Vinyl quinone methides 4a and 4b were obtained in high yields by Ag2O oxidation of eugenol (3a) and of 2,6-dimethoxy-4-(2-propenyl)phenol (3b).Vinyl quinone methides (VQMs) reacted with alcohols, with phenols, and with acetic acid giving compounds 5 and 6.As the former rearranged to the latter in the reaction medium, the addition of the reported substrates to VQMs turned out to be wholly regioselective toward the formation of coniferyl and sinapyl derivatives 6.In contrast, addition of carbon nucleophiles (acetylacetone and EtNO2) to VQMs gave both compounds 7 and 8.By reaction of the acetates 6a and 6b (CR=CH3CO) with LiAlH4 it was possible to perform a novel synthesis of coniferyl and sinapyl alcohols (1a and 1b).Treatment of the same acetates with an aqueous solution of NaHCO3 reproduced VQMs 4, which by subsequent reduction with NaBH4, gave propenylphenols 2 and allylphenols 3.Formation of the latter compounds from coniferyl and sinapyl acetates via VQM is here proposed as a possible biosynthetic pathway.
- Zanarotti, Antonio
-
p. 941 - 945
(2007/10/02)
-
- Glycosides of 2,6-bis(hydroxy-phenyl)-3,7-dioxabicyclo [3,3,0] octane
-
Mono- and di-glycosides of 2,6-bis (hydroxy-phenyl)-3,7-dioxabicyclo [3,3,0] octane and methods for preparing such compounds. The compounds exhibit anti-hypertensive properties.
- -
-
-