Chemistry: electrical and wave energy – Processes and products – Electrostatic field or electrical discharge
Patent
1981-03-02
1982-08-24
Gerstl, Robert
Chemistry: electrical and wave energy
Processes and products
Electrostatic field or electrical discharge
560121, 562503, 568591, 424305, 424317, 549533, C07C30116
Patent
active
043459846
ABSTRACT:
A novel process for the oxidation of olefins to the corresponding alpha-epoxy alcohols which can be incorporated in the total synthesis of members of a novel class of prostaglandin analogues.
Olefins are reacted with singlet oxygen in the presence of a group IVB, VB or VIB transition metal catalyst, excluding chromium. The reaction is fast and highly selective to the alpha-epoxy alcohol. When cyclopentene is oxidized in the process of the invention, high yields of cis 2,3-epoxy-cyclopentan-1-ol are obtained. The latter compound is used as a starting material in the synthesis of prostaglandin analogues. The prostanoids of the invention are characterized by an oxa group replacing the methylene group at the 7-position, and the absence of a hydroxyl or other substituent at the 11-position.
Members of this class of prostanoids show important cytoprotective properties in animal tests.
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Gerstl Robert
Goldstein Steven J.
Schaeffer Jack D.
The Procter & Gamble & Company
Witte Richard C.
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