Prostaglandin synthesis and intermediates for use therein
US8309744B2 · kind B2 · utility
Assignee
Inventors
Key dates
| Filing date | Apr 7, 2011 |
| Grant date | Nov 13, 2012 |
| Priority date | — |
| Expiry date | Apr 7, 2031 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07C2601/08
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
Fused cyclopentane—4-substituted 3,5-dioxalane lactone compounds useful as an intermediate in the synthesis of prostaglandin analogs are provided. The compounds have the formula A:wherein R represents an aryl group such as p-methoxyphenyl.This compound can be reacted with a lower alkyl aluminum compound to open the dioxalane ring and reduce the lactone to lactol, without over-reducing to diol. The resulting compound can be functionalized to insert chemical side groups of target prostaglandins, adding the required α-side chain and then the required ω-side chain sequentially and independently of each other. The compounds and process are particularly suitable for preparing lubiprostone.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.