85539-94-2

Upstream product

• 54125-02-9 danishefsky's diene 
• 6776-19-8 ethyl (Z)-crotonate 
• 4341-76-8 Ethyl 2-butynoate 

Downstream Products

• 95218-47-6 (4R,5R)-4-Hydroxymethyl-5-methyl-cyclohex-2-enone 
• 85539-95-3 (4RS,5RS)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-5-methylcyclohex-2-en-1-one 
• 95218-50-1 (3RS,4SR,5SR)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-3-methoxy-5-methylcyclohexanone 
• 85539-97-5 (3RS,4RS,5RS)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-3-methyl-5-<<3,3-(propylenedioxy)propyl>-1,3-dithian-2-yl>cyclohexanone 
• 95218-67-0 (1SR,2SR,8aRS)-8-(1,3-dithian-2-yl)-2-methyl-1-<<(S)-(O-methylmandelyl)oxy>methyl>-4-oxo-1,2,3,4,6,7,8,8a-octahydronaphthalene 
• 95218-58-9 (1SR,2SR,8SR,8aRS)-2-methyl-8-<(2-methoxyethoxy)methoxy>-1-<(triphenylphosphonio)methyl>-1,2,6,7,8,8a-hexahydronaphthalene iodide 

Relevant academic research and scientific papers

SYNTHESIS AND BIOLOGICAL ACTIVITY OF THE HEXALIN MOIETY OF COMPACTIN (ML-236B)

Alcohols 14 and 21 and the derived half-glutarate esters 15 and 22 have been prepared and evaluated as inhibitors of HMG CoA reductase.Compound 14, the hexalin moiety of the natural fungal metabolite compactin (ML-236B) and compound 21, its isomeric diene, have essentially no inhibitory properties.Compound 15 and 22 show definite activity, although several orders of magnitude lower than that shown by compactin.

Synthetic and Biological Studies of Compactin and Related Compounds. 3. Synthesis of the Hexalin Portion of Compactin

Several synthons for the hexalin moiety of compactin (1) have been prepared, and a procedure for production of the key alcohol 5 in enantiomerically homogeneous form is presented.Diels-Alder reaction of ethyl (Z)-crotonate and Danishefsky's diene affords cycloadduct 6 (78percent).Hydride reduction followed by silylation of the resulting primary alcohol gives enone 8 (72percent).Two-step cyclohexene annelation furnishes enone 11 (42-55percent), which is elaborated to diene 21 by using a modification of the Shapiro olefin synthesis (three steps, 60percent).Dithiane hydrolysis followed by L-Selectride (Aldrich) reduction of the resulting ketone affords axial alcohol 28.Compound 28 possesses the correct relative stereochemistry at the four contiguous asymmetric carbon atoms in the hexalin portion of 1, and the synthesis is suitable for large-scale preparation (ten steps, 10-14 percent, no isomer separations).Functional group manipulations give synthons 36-39.Acid-catalyzed dehydration of allylic alcohol 19 affords diene isomer 20 (11:1).A simple procedure for the preparation of large quantities of ethyl (Z)-crotonate is also presented.