C16 unsaturated FP-selective prostaglandins analogs
A kind of technology selected from, compound, be applied in described new prostaglandin F analog, new prostaglandin F analog field
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Embodiment 1
[0058] 13,14-Dihydro-16-17-Z-didehydro-17-(2-fluorophenyl)prostaglandin F 1α preparation of a. Methyl 7-(2-oxo-4-(1,1,2,2-tetramethyl-1-silapropoxy)cyclopent-1-enyl)heptanoate (E1b):
[0059] CH 2 Cl 2 2,6-Lutidine (1.3 equivalents) was added dropwise to the solution over 15 minutes. The solution was incubated at -78°C. TBDMS triflate (Triflate) (1.2 equiv) in CH 2 Cl 2 solution. The reaction was gradually warmed to room temperature and stirred at room temperature for 15 hours. 10% aqueous HCl solution was added, and the layers were separated. use CH 2 Cl 2 The aqueous layer was extracted, and the organic layers were combined. The organic layer was washed with brine, dried (Na 2 SO 4 ), and condensed. The residue was distilled under vacuum (10 mmHg) to obtain silyl ether E1b. b. 7-(5-but-3-enyl-2-hydroxyl-4-(1,1,2,2-tetramethyl-1-silapropoxy)cyclopentyl)heptanoic acid methyl ester ( E1c):
[0060] To a THF slurry of Mg powder (2 eq.) was added crystalline iod...
Embodiment 2-17
[0067] Examples 2-17 were prepared with reference to Example 1, substituting appropriate starting materials. Those skilled in the art can appropriately change the temperature, pressure, atmosphere, solvent or sequence of the reaction. In addition, those skilled in the art can appropriately use protecting groups to block side reactions or increase yield. All of the above modifications can be readily carried out by a skilled organic chemist and, therefore, fall within the scope of the present invention.
Embodiment 2
[0069] 13,14-Dihydro-16-17-E-didehydro-17-(2-fluorophenyl)-17-trinorprostaglandin F1α
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