14719-32-5Relevant academic research and scientific papers
First total synthesis of Debilisone C
Saikia, Bishwajit,Joymati Devi, Thongam,Barua, Nabin C.
, p. 905 - 913 (2013/03/14)
Total synthesis of Debilisone C, a lactone containing conjugated endiyne has been achieved. The adopted strategy involves the stereoselective construction of the five membered lactone ring and the C20 endiyne chain followed by regioselective coupling of both the parts. The lactone was obtained from the oxidative cleavage of the hydroxy olefin which was derived from the benzyl protected S-epichlorohydrine by regioselective epoxide opening with allyl trimethyl silane in presence of a Lewis acid at -78 °C. Takai olefination, Pd0/Ag1 catalyzed cross-coupling reaction and selective substitution of trimethylsilyl groups were successfully utilized to establish the C20 polyyne chain. The final coupling of both the parts have been carried out by alkyl coupling using LDA in THF-DMPU (1 : 1).
Regiocontrolled formation of iodohydrins and epoxides from Vic-diols
Adiyaman,Khanapure,Hwang,Rokach
, p. 7367 - 7370 (2007/10/02)
A novel method for the stereoselective preparation of iodohydrins and epoxides from stereogenic vicinal diols is described. This new high-yield methodology consists of the conversion of thionocarbonates such as 12 to the primary iodo derivative 14 with complete regiocontrol. Deprotection of ther secondary alcohol derivative in 14 gives the corresponding synthetically versatile iodohydrin 16, which is converted to epoxide 17. This methodology has been applied to complex tetraols 29 and 34. In the case of diols the transformation is conveniently carried out in high yield as a one-pot reaction.
