Process for preparing a 2(R) or 2(S) tricyclic lactone glycol
AssigneeThe Upjohn Company
InventorVerlan H. Van Rheenen
Life of this patent
Estimating the term…
Abstract
A process for preparing optically active 2(S) or 2(R) tricyclic lactone glycols of the formula ##STR1## wherein W is 1-pentyl, 1-pent-cis-2-enyl, or 1-pent-2-ynyl. This process is useful for preparing stereospecifically prostaglandins having pharmacological utility.
Claims6
A process for preparing an optically active 2S tricyclic lactone glycol of the formula ##STR2## or a racemic compound of that formula and the mirror image of that formula, wherein W is 1-pentyl, cis 1-pent-2-enyl, or 1-pent-2-ynyl, and .about. indicates attachment of the hydroxyl to the side chain in alpha or beta configuration, which comprises starting with an optically active 2R tricyclic lactone glycol of the formula ##STR3## or a racemic compound of that formula and the mirror image of that formula, wherein W and .about. are as defined above, and subjecting said 2R glycol successively to the following reactions:
- A. monosulfonation to replace the hydrogen of the C-2 hydroxyl with a sulfonyl group of the formula --SO.sub.2 --R.sub.3 wherein R.sub.3 is alkyl of one to 10 carbon atoms, inclusive, aralkyl of 7 to 12 carbon atoms, inclusive, phenyl or phenyl substituted with one or 2 halo or alkyl groups of one to 4 carbon atoms, inclusive:
- B. acylation to replace the hydrogen of the C-1 hydroxyl with an acyl group of the formula --C(O)--R.sub.4 wherein R.sub.4 is alkyl of one to 10 carbon atoms, inclusive, aralkyl of 7 to 12 carbon atoms, inclusive, phenyl or phenyl substituted with one or 2 halo or alkyl groups of one to 4 carbon atoms, inclusive;
- c. transformation of the product of step b to an optically active 2 S compound of the formula ##STR4## or a racemic compound of that formula and the mirror image of that formula, wherein one of E and M is hydrogen and the other is an acyl group of the formula --C(O)R.sub.4 wherein R.sub.4 is as defined above, wherein .about. indicates attachment of the moiety to the side chain in either alpha or beta configuration, and wherein W is as defined above;
- and
- d. replacement of the acyl group --C(O)R.sub.4 with hydrogen.
A process preparing an optically active 2R tricyclic lactone glycol of the formula ##STR5## or a racemic compound of that formula and the mirror image of that formula, wherein W is 1-pentyl, cis 1-pent-2-enyl, or 1-pent-2-ynyl, and .about. indicates attachment of the hydroxyl to the side chain in alpha or beta configuration, which comprises starting with an optically active 2S tricyclic lactone glycol of the formula ##STR6## or a racemic compound of that formula and the mirror image of that formula, wherein W and .about. are as defined above, and subjecting said 2S glycol successively to the following reactions:
- a. monosulfonation to replace the hydrogen of the C-2 hydroxyl with a sulfonyl group of the formula --SO.sub.2 --R.sub.3 wherein R.sub.3 is alkyl of one to 10 carbon atoms, inclusive, aralkyl of 7 to 12 carbon atoms, inclusive, phenyl or phenyl substituted with one or 2 halo or alkyl groups of one to 4 carbon atoms, inclusive:
- b. acylation to replace the hydrogen of the C-1 hydroxyl with an acyl group of the formula --C(O)--R.sub.4 wherein R.sub.4 is alkyl of one to 10 carbon atoms, inclusive, aralkyl of 7 to 12 carbon atoms, inclusive, phenyl or phenyl substituted with one or 2 halo or alkyl groups of one to 4 carbon atoms, inclusive;
- c. transformation of the product of step b to an optically active 2R compound of the formula ##STR7## or a racemic compound of that formula and the mirror image of that formula, wherein one of E and M is hydrogen and the other is an acyl group of the formula --C(O)R.sub.4 is as defined above, wherein .about. indicates attachment of the moiety to the side chain in either alpha or beta configuration, and wherein W is as defined above;
- and
- d. replacement of the acyl group --C(O)R.sub.4 with hydrogen.
Dependencies are inferred from the claim text.