Organic compounds -- part of the class 532-570 series – Organic compounds – Sulfur containing
Patent
1985-08-19
1988-03-22
Gerstl, Robert
Organic compounds -- part of the class 532-570 series
Organic compounds
Sulfur containing
546340, 549 78, C07C17700
Patent
active
047330112
ABSTRACT:
Compounds of the formula ##STR1## wherein A is C--C single bond, --CH.sub.2 --, --CH(CH.sub.3)--, --C(CH.sub.3).sub.2 --, --CH.sub.2 --CH.sub.2 --, CH(CH.sub.3)CH.sub.2 --, --C(CH.sub.3).sub.2 CH.sub.2 --, --CH.sub.2 --CH.sub.2 --CH.sub.2 -- or --CH.sub.2 O--; R.sup.1a and R.sup.1 each independently is hydrogen or a protective group which can be cleaved by solvolysis or by hydrogenolysis; R.sup.2 is H or alkyl of 1 to 3 C atoms; R.sup.3 is alkyl of 3 to 5 C atoms, phenyl or phenyl which is monosubstituted to trisubstituted by F, Cl, OH, OCH.sub.3, OC.sub.2 H.sub.5, CF.sub.3 or alkyl of 1 to 3 C atoms, or, when A is not --CH.sub.2 O--, can also be pyridyl, thienyl, naphthyl or alkoxy of 1 to 4 C atoms; indicates a bond in the .beta.-position and wavy line ( ) means that the bond can be in the .alpha.- or .beta.-position, are valuable intermediates for the stereospecific preparation of 13-thiaprostaglandin derivatives. The latter are prepared by U.V. irradiation of the former to first prepare the corresponding 2-oxa-3-OH-6-alkylthio-7-OH-1,5-bicyclo(3.3.0)octane derivative, which is then exposed to a Wittig reaction and, optionally, hydrogenation or oxidation inter alia to prepare members of the F.sub.1 -, F.sub.2 -, E.sub.1 - and E.sub.2 series.
REFERENCES:
patent: 4272629 (1981-06-01), Roberts
Morton et al, Adv. Photochem. 1974, 9, 197.
Radunz Hans-Eckart
Riefling Bernhard
Gerstl Robert
Merck Patent Gesellschaft mit beschrankter Haftung
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