Prostaglandin F series

This compound has not been previously reported in the literature. The compound is unusual In that the substitution pattern of alkyl and hydroxyl groups on the ring Is analogous to the prostaglandin F series. 

Contraction of the non-pregnant uterus Induction of abortion and labor Prostaglandin F series... 

DINOPROST (Prostaglandin Fj) The Prostaglandin F-series provokes contraction of bronchial, intestinal and pregnant uterine muscles. Therefore dinoprost is used clinically to terminate pregnancy in the first and second trimester. 

Dichloroketene reacted with (185) to form the gem-dichlorocyclobutanone (186), which could be transformed to the important intermediates (188) and (191) for the synthesis of prostaglandins A and F series 66,54). 

Release of oxytocin at this stage of parturition promotes prostaglandin production, particularly of the E and F series, within the decidua these prostaglandins are powerful myometrial stimulants and thus further enhance uterine contractions. The prostaglandin concentration in maternal serum and amniotic fluid increases with the progression of labor. 

Cimino, G. Crispino, A. Di Marzo, V. Spinella, A. Sodano, G. (1991) Prostaglandin 1,15-lactones of the F series from the nudibranch mollusc Tethys fimbria. J. Org. Chem., 56,2907-11. 

Ellman utilized the Suzuki coupling twice between a support-bound vinyl bromide and an alkyl 9-BBN derivative in a solid-phase synthesis of E- and F-series prostaglandins. The Suzuki reaction was performed in situ, with the hydroboration of a terminal olefin being followed by the palladium-mediated step. This sequence is attractive in library synthesis because of the wide range of suitable commercially available alkenes. The inspiration behind this chemistry was the solution-phase work of Johnson and Braun, where the couplings of 35 with 2-iodo-4-(silyloxy)cyclopent-2-enone 36 went well at room temperature with PdCljCdppO-AsPhj as catalyst (Scheme 41). The modular chemistry demonstrated in this paper was clearly amenable to adaptation to a solid-phase strategy. 

Yin K, Hahishka PV, Yan Y-T, Wong PY-K. Antiaggregatory activity of 8-epi-prostaglandin Fj, and other F-series prostanoids and their binding to thromboxane Aj/ prostaglandin receptors in human platelets. J Pharmacol Exp Ther 1994 270 1192-6... 

MS and GC-MS. A variety of derivatives have been used to protect labile functional groups of the free prostaglandins prior to gas chromatography and direct fragmentation in GC-MS. The 9,11-/3-ketol grouping of the E series is particularly sensitive in vapour phase analysis and commonly 0-methyloxime TMS ether derivatives or O-methyloxime acetates have been employed in GC-MS (e.g. [426]). An alternative approach is to dehydrate the ketol under controlled conditions to the more stable enone analogues of the B series [427,428]. The cyclic n-butylboronate of the 9,11-diol in the F series when used with methyl ester TMS ethers confers good GC properties and some simplification in... 

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