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US 2003/0191095 A1Published application
Method of synthesizing 1alpha-hydroxy-2-methylene-19-nor-homopregnacalciferol
AssigneeWisconsin Alumni Research Foundation
InventorsHector F. DeLuca, Sumithra Gowlugari, Rafal R. Sicinski
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Abstract
A method of making 1α-hydroxy-2-methylene-19-nor-homopregnacalciferol. The method includes the steps of condensing a bicyclic ketone with an allylic phosphine oxide to produce a protected 19-nor-pregnacalciferol analog, thereafter cleaving the protecting group to form 22-alcohol, converting the alcohol to an ester, reducing the ester to 17β-isopropyl-19-nor-vitamin D analog, and finally deprotecting the 17β-isopropyl derivative to form the desired compound.
Claims15
A method of making 1α-hydroxy-2-methylene-19-nor-homopregnacalciferol having the structure
- 13
- comprising the steps of:
- condensing a bicyclic ketone having the structure
- 14
- with an allylic phosphine oxide having the structure
- 15
- where Y1, Y2 and R, which may be the same or different, are each a hydroxy-protecting group, to produce a protected 19-nor-pregnacalciferol analog having the structure
- 16
- thereafter cleaving the protecting group R to form 22-alcohol having the structure
- 17
- converting said 22-alcohol to an ester having the structure
- 18
- where R1 is a tosyl group or a mesyl group;
- reducing said ester to obtain 17β-isopropyl-19-nor-vitamin D analog having the structure
- 19
- and deprotecting said 17β-isopropyl vitamin D derivative to form 1α-hydroxy-2-methylene-19-nor-homopregnacalciferol.
13 more elements
Dependencies are inferred from the claim text.