833476-69-0

Upstream product

• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 833476-48-5 (E)-(4R,5R)-5-(4-Bromo-phenyl)-5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pent-2-enal 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 1122-91-4 4-bromo-benzaldehyde 
• 833476-46-3 (R)-3-[(E)-(4R,5R)-5-(4-Bromo-phenyl)-5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pent-2-enoyl]-4-isopropyl-oxazolidin-2-one 
• 833476-66-7 (R)-3-[(E)-(4R,5R)-5-(4-Bromo-phenyl)-5-hydroxy-2,4-dimethyl-pent-2-enoyl]-4-isopropyl-oxazolidin-2-one 
• 833476-42-9 (4R,1'E,3'E)-(-1'-{[tert-butyl(dimethyl)silyl]oxy}-2'-methyl-1',3'-pentadienyl)-4-isopropyl-1,3-oxazolidin-2-one 

Downstream Products

• 157479-37-3 trichostatin D 
• 833476-50-9 (2E,4E)-(6R,7R)-7-(4-Bromo-phenyl)-7-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hepta-2,4-dienoic acid 

Relevant academic research and scientific papers

Stereo- and Enantioselective Synthesis of Propionate-Derived Trisubstituted Alkene Motifs

We report a new method for constructing propionate-derived trisubstituted alkene motifs in a stereoselective manner. 1-Substituted 1,1-di(pinacolatoboryl)-(E)-alk-2-enes are generated in situ from 1-substituted 1,1-di(pinacolatoboryl)alk-3-enes through ruthenium(II)-catalyzed double-bond transposition. These species undergo a chiral phosphoric acid catalyzed allylation reaction of aldehydes to produce the E isomers of anti-homoallylic alcohols. On the other hand, the corresponding Z isomers of anti-homoallylic alcohols are obtained when a dimeric palladium(I) complex is employed as the catalyst for this double-bond transposition. Thus, both E and Z isomers can be synthesized from the same starting materials. A B?C(sp2) bond remaining with the allylation product undergoes the Suzuki–Miyaura cross-coupling reaction to furnish a propionate-derived trisubstituted alkene motif in a stereo-defined form. The present method to construct the motifs with (E)- and (Z)-alkenes are successfully applied to the syntheses of (+)-isotrichostatic acid, (?)-isotrichostatin RK, and (+)-trichostatic acid, respectively.

The first total synthesis of trichostatin D

Trichostatin D and 6-epi-trichostatin D have been stereoselectively synthesized through a remote stereoinduction with a chiral vinylketene silyl N,O-acetal and glycosylation of hydroxyimide under Mitsunobu conditions.