Process for the preparation of 4-hydroxycyclopent-2-en-1-one der

Details Process for the preparation of 4-hydroxycyclopent-2-en-1-one der Process for the preparation of 4-hydroxycyclopent-2-en-1-one der

1975-12-22

1979-01-02

Shaver, Paul F.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2603459P, 260463, 260586R, 260590C, 568838, 568667, 560262, 560106, 560 60, C07F 718

Patent

active

041327268

ABSTRACT:
Novel optically active compounds of 4-protected hydroxy-cyclopent-2-en-1-ones of the formula ##STR1## wherein R is a splittable protective group for an alcoholic hydroxyl group, and a process for preparing the 4-protected hydroxycyclopent-2-en-1-ones by oxidizing monohydroxy-protected derivatives of cyclopent-1-ene-3,5-diol expressed by the following formula ##STR2## wherein R is the same as defined above. Optically active 4-hydroxycyclopent-2-en-1-one which is an optically active isomer of the compound of formula (2); or optically active cyclopent-1-en-3,5-diol (R-isomer) and a novel diacyl derivative of the diol, a novel monoacylmonosilyl-derivative of the diol and a novel monoacylmonotetrahydropyranol-derivative of the diol, which are intermediates for the protective derivative of formula (1). Processes are also provided for preparing the protective derivatives of formula (1) by converting these intermediates by esterification, hydrolysis, enzymatic processes, etc. The optically active compounds of formula (2) are useful as precursors for the preparation of prostaglandin or its analogues.

REFERENCES:
patent: 2951057 (1960-08-01), Wiese et al.
patent: 2957901 (1960-10-01), Olson et al.
patent: 2974157 (1961-03-01), Jex
patent: 3843704 (1974-10-01), Hetzel
patent: 3852097 (1974-12-01), Owen et al.
patent: 3856843 (1974-12-01), Nagai et al.
patent: 3922436 (1975-11-01), Bell et al.
patent: 3954835 (1976-05-01), Samuelson et al.

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