156624-89-4

Upstream product

• 121103-78-4 methyl (2S,3S,E)-3-hydroxy-2,4-dimethyl-5-phenylpent-4-enoate 
• 15174-47-7 α-methyl-trans-cinnamaldehyde 
• 156624-87-2 (E)-(2S,3S)-3-Hydroxy-2,4-dimethyl-5-phenyl-pent-4-enethioic acid S-phenyl ester 
• 156624-88-3 tert-butyl (4S,5S,E)-5-hydroxy-4,6-dimethyl-3-oxo-7-phenylhept-6-enoate 

Downstream Products

• 156624-91-8 (4S,5S,6S)-5-Methyl-6-((E)-1-methyl-2-phenyl-vinyl)-4-triisopropylsilanyloxy-tetrahydro-pyran-2-one 
• 156624-90-7 (4S,5R,6S)-4-hydroxy-5-methyl-6-((E)-1-phenylprop-1-en-2-yl)tetrahydro-2H-pyran-2-one 

Relevant academic research and scientific papers

Ni-Catalyzed chemoselective alcoholysis of: N -acyloxazolidinones

Although N-acyloxazolidinone-based (catalytic) asymmetric synthetic methodologies occupy an important position in modern organic synthesis, the catalytic cleavage of a chiral auxiliary remains underdeveloped. We report the Ni(cod)2/bipyr.-catalyzed alcoholysis of N-acyloxazolidinones to deliver esters. The reaction is broad in scope for both N-acyloxazolidinone substrates and alcohol nucleophiles, and displays good functional group tolerance and excellent chemoselectivity. A gram-scale methanolysis allowed the enantioselective synthesis of the C22-C26 segment of a close analogue of the potent immunosuppressant agent FK506.

Total syntheses of close analogues of the immunosuppressant FK506

The total synthesis of an analogue of FK506, in which the substituted cyclohexyl residue at C28 has been replaced by a phenyl group, is described. This synthesis demonstrates (i) the successful application of new methodology for the introduction of the masked tricarbonyl grouping (C8-C10), and (ii) new synthetic routes to the (C10-C19) and (C22-C26) regions.