Prostaglandins and Congeners. 27. Synthesis of Biologically Active 16-Halomethyl Derivatives of 15-Deoxy-16-hydroxyprostaglandin E2

Article abstract of DOI:10.1021/jo01300a002

The 16-CF3, -CHF2, -CH2F, and -CH2Cl derivatives of DL-15-deoxy-16-hydroxyprostaglandin E₂ (8a, 8b, 8c, and 8d, respectively) were prepared by conjugate addition of the lithiocuprates derived from the appropriately functionalized vinylstannanes 4 to cyclopentenone 6.Hydrolysis of the rather stable O-Si linkage at C-16 of the prostaglandin is discussed.The 13C-NMR chemical shifts of the prostaglandin analogues and intermediates are noted.