The synthesis of novel prostaglandin analogues via cycloaddition reactions

The total synthesis of the cyclobutane prostaglandin analogues (4) and (5), and their subsequent conversion to the γ-lactones (6) and (7), γ-lactam (8) and cyclopentanone (9) is described. The cornerstone of the synthetic strategy is the intermolecular [2 + 2] cycloaddition of dichloroketene to a suitably functionalised enol ether.

[1]  K. Sharpless,et al.  Arenesulfonate derivatives of homochiral glycidol: versatile chiral building blocks for organic synthesis , 1989 .

[2]  R. Bittman,et al.  A two-step synthesis of (R)- and (S)-benzylglycidyl ether , 1989 .

[3]  K. Sharpless,et al.  Catalytic asymmetric epoxidation and kinetic resolution: modified procedures including in situ derivatization , 1987 .

[4]  Son Sj.  Prostaglandins and acid peptic disease. , 1986 .

[5]  K. Sharpless,et al.  Asymmetric epoxidation of allyl alcohol: efficient routes to homochiral .beta.-adrenergic blocking agents , 1986 .

[6]  K. Vijayakumaran,et al.  Pyridinium dichromate oxidation. Modifications enhancing its synthetic utility , 1985 .

[7]  S. Ohkawa,et al.  Thromboxane synthetase inhibitors (TXSI). Design, synthesis, and evaluation of a novel series of omega-pyridylalkenoic acids. , 1985, Journal of medicinal chemistry.

[8]  A. Greene,et al.  Asymmetric induction in the cycloaddition reaction of dichloroketene with chiral enol ethers. A versatile approach to optically active cyclopentenone derivatives. , 1985 .

[9]  S. Ito,et al.  Microscopic analysis of ethanol damage to rat gastric mucosa after treatment with a prostaglandin. , 1982, Gastroenterology.

[10]  T. Shioiri,et al.  New Methods and Reagents in Organic Synthesis. 18. Homologation of Ketones with Trimethylsilyldiazomethane (TMSCHN2) , 1982 .

[11]  Antoni Costa,et al.  Reactions on Silica Gel. Beckmann Rearrangement of Oxime p-Toluenesulfonates , 1982 .

[12]  W. T. Brady.  Synthetic applications involving halogenated ketenes , 1981 .

[13]  A. Greene,et al.  Synthesis of ring modified prostaglandins , 1981 .

[14]  P. Collins,et al.  Synthesis and gastric antisecretory properties of 15-deoxy-16-hydroxyprostaglandin E analogues. , 1977, Journal of medicinal chemistry.

[15]  E. J. Grubbs,et al.  The Reaction of Ketones with Diazomethane , 1960 .