Claims
- 1. A compound of the formula ##STR6## wherein A is a 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 with an acid or a base or by catalytic 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 or 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 a wavy line ( ) means that the bond can be in the .alpha.- or .beta.-position.
- 2. A compound of claim 1 wherein A=--CH.sub.2 --, --CH(CH.sub.3)-- or --C(CH.sub.3).sub.2 -- and R.sup.3 =butyl.
- 3. A compound of claim 1 wherein A=--CH.sub.2 --, --CH(CH.sub.3)-- or --C(CH.sub.3).sub.2 --, R.sup.2 =methyl and R.sup.3 =butyl.
- 4. A compound of claim 1 wherein A =--CH.sub.2 --CH.sub.2 or --CH.sub.2 O-- and R.sup.3 =phenyl, 3-chlorophenyl, 3-trifluoromethylphenyl or 3-methoxyphenyl.
- 5. A compound of claim 1 wherein A=--CH.sub.2 --CH.sub.2 -- or --CH.sub.2 O--, R.sup.2 =H or methyl and R.sup.3 =phenyl, 3-chlorophenyl, 3-trifluoromethylphenyl or 3-methoxyphenyl.
- 6. A compound of claim 1 wherein A=--CH.sub.2 --CH.sub.2 -- or --CH.sub.2 O--, R.sup.1 =H, R.sup.2 =H or methyl and R.sup.3 =phenyl, 3-chlorophenyl, 3-trifluoromethylphenyl or 3-methoxyphenyl.
- 7. 3.alpha.-Hydroxy-2.beta.-(3-(3-chlorophenoxy)-2-hydroxypropylthio)-1.beta.H,5.beta.H-bicyclo[3.2.0]heptan-6-one, a compound of claim 1.
- 8. 3.alpha.-Hydyroxy-2.beta.-(2-hydroxy-2-methyl-heptylthio)bicyclo[3.2.0]heptan-6-one, a compound of claim 1.
- 9. A compound of claim 1 wherein R.sup.2 is H .
- 10. A compound of claim 1 wherein R.sup.2 is alkyl.
- 11. A compound of claim 1 wherein A is --CH.sub.2 O--.
- 12. A compound of claim 1 wherein R.sup.3 is alkyl.
- 13. A compound of claim 1 wherein R.sup.3 is pyridyl, thienyl, or naphthyl.
- 14. A compound of claim 1 wherein R.sup.3 is phenyl or substituted phenyl.
- 15. A process for preparing a compound regiospecifically in the 2.beta.-position, the compound being of the formula ##STR7## wherein A is a 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 with an acid or a base or by catalytic 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, C1, 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 .alpha.-position, indicates a bond in the .beta.-position and a wavy line means that the bond can be in the .alpha.-or .beta.-position
- comprising reacting, under basic conditions the corresponding 2 .beta.-bromo-3.alpha.-hydroxy-bicyclo [3.2.0]heptan-6-one, with retention of configuration, at the 2- and 3-positions,
- with a thiol or thiolate of the formula ##STR8## wherein M is H, one equivalent of a metal atom or an ammonium ion and A and R.sup.1 to R.sup.3 are as defined above.
- 16. A process of claim 15 wherein said heptanone reactant has the configuration 2.beta., 3.alpha.-.
- 17. A process of claim 15 further comprising blocking one or more hydroxy groups on the product of said reaction by a protective group which can be cleaved by solvolysis with an acid or a base or by catalytic hydrogenolysis.
Priority Claims (1)
Number |
Date |
Country |
Kind |
3025325 |
Jul 1980 |
DEX |
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Parent Case Info
This is a division, of application Ser. No. 280,191 filed July 6, 1981 now abandoned.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
4272629 |
Roberts |
Jun 1981 |
|
Foreign Referenced Citations (1)
Number |
Date |
Country |
1072549 |
Feb 1980 |
CAX |
Non-Patent Literature Citations (1)
Entry |
Morton et al, Adv. Photochem. 1974, 9, 197. |
Divisions (1)
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Number |
Date |
Country |
Parent |
280191 |
Jul 1981 |
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