Stereoselective synthesis of 24-hydroxylated compounds useful for the preparation of aminosterols, vitamin D analogs, and other compounds
US6262283A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Dec 5, 1997 |
| Grant date | Jul 17, 2001 |
| Priority date | — |
| Expiry date | Dec 5, 2017 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07J41/0005
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
A method is described for stereoselectively reducing an unsaturated alkyl ketone substituent attached to a fused ring base. In this method, the unsaturated alkyl ketone reacts with a chiral oxazaborolidine reagent. This reaction stereoselectively reduces the unsaturated alkyl ketone to an unsaturated alkyl alcohol. The unsaturated alkyl alcohol can be further reduced, if desired, to produce a saturated alkyl alcohol. The fused ring base can be, for example, a steroid ring base or a base of a vitamin D analog. The process in accordance with the invention can be used with an alkeneone substituent (e.g., a 22-ene-24-one substituent) or an alkyneone substituent (e.g., a 22-yne-24-one substituent) on a steroid ring base to make squalamine or other useful aminosterol compounds and intermediates for making aminosterol compounds.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.