605674-54-2

Upstream product

• 71945-73-8 4-(2-hydroxy-4-methylphenyl)-butyric acid 
• 59010-46-7 4-(2-Hydroxy-4-methylphenyl)-4-oxobutanoic Acid 
• 145964-98-3 2-methoxy-ω-bromo-4-methylacetophenone 
• 108-39-4 3-methyl-phenol 
• 105402-00-4 4-(2-methoxy-4-methylphenyl)butyric acid 
• 74-88-4 methyl iodide 

Relevant academic research and scientific papers

Synthesis of (+/-)-hamigeran B, (-)-hamigeran B, and (+/-)-1-epi-hamigeran B: use of bulky silyl groups to protect a benzylic carbon-oxygen bond from hydrogenolysis.

Enone 42 was converted into diene 56, which was then subjected to hydrogenation. Use of the tert-butyldimethylsiloxy groups enforces facial selectivity and protects the C(5) oxygen from hydrogenolysis. The resulting product (55) is easily converted into hamigeran B (1), a marine natural product with powerful activity against herpes and polio viruses. Optically pure enone 73 was made by use of a Meyers' auxiliary and converted into (-)-hamigeran B with the natural absolute configuration.

Stereospecific total synthesis of the antiviral agent hamigeran B - Use of large silyl groups to enforce facial selectivity and to suppress hydrogenolysis

Stereoselective hydrogenation of the tetrasubstituted double bond in enone 1 is possible, provided the keto group at C7 is first removed and the α face is blocked by tert-butyldimethylsiloxy groups at positions 10 and 11. The resulting product 2 is easily