79399-53-4Relevant academic research and scientific papers
Allylic sulfones containing triene moieties as key synthons for carotenoid synthesis
Ji, Minkoo,Choi, Hojin,Jeong, Young Cheol,Jin, Jingquan,Baik, Woonphil,Lee, Sijoon,Kim, Jeong Soo,Park, Minsoo,Koo, Sangho
, p. 2620 - 2628 (2003)
An efficient synthetic method for the allylic sulfone 2 containing a conjugated triene moiety has been proposed involving i) coupling of allylic sulfones 4 with the C5 bromoallylic sulfide 5, ii) base-promoted dehydrosulfonation in the presence of allylic sulfide, and iii) selective oxidation of the resulting trienyl sulfide to the corresponding sulfone. Total synthesis of lycopene starting from the C15 allylic sulfone 2b has been described, where the new C10 bis(chloroallylic) sulfone 11 proved to be a useful substitute for the C10 bis(chloroallylic) sulfide 3, which did not require the problematic chemoselective sulfur oxidation in a conjugated polyene.
THE MICHAEL INDUCED RAMBERG-BAECKLUND HOMOLOGATION TO CONJUGATED ISOPRENOIDS
Burger, J. J.,Chen, T. B. R. A.,Waard, E. R. de,Huisman, H. O.
, p. 417 - 424 (2007/10/02)
Treatment of the sulfones 1 or 2 with sodium phenylsulfinate in DMSO affords the head-to-tail coupled conjugated monoterpenoids 5-8 in comparable amounts.The correspondig reaction of 3 gives the isomers 16 and 17.The tail-to-tail homologation of 4 furnishes chiefly a 2E,4E/Z mixture of the conjugated isoprenoids 18 and 19.The various isoprenoid mixtures are separated into their components and the configuration of the isomers is established by (1)H NMR double resonance and the NMR/NOE technique.The head-to-tail and tail-to-tail coupled isoprenoid mixtures 5-8 and 18-21, respectively, are isomerized to 2E/Z,4E-mixtures in a 2:1 ratio.The C15 sulfones 11 and 13 are obtained by treatment of 1 with the head-functionalized isoprene synthon 10.Some speculations on the stereochemical course of the MIRB-homologation are presented.
