Prostaglandin synthesis and intermediates for use therein

C - Chemistry – Metallurgy – 07 – D

Patent

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Details

C07D 493/04 (2006.01) C07C 405/00 (2006.01) C07D 307/935 (2006.01) C07D 311/94 (2006.01)

Patent

CA 2639240

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: (see 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 .alpha.-side chain and then the required .omega.-side chain sequentially and independently of each other. The compounds and process are particularly suitable for preparing lubiprostone.

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