PROSTAGLANDIN SYNTHESIS AND INTERMEDIATES FOR USE THEREIN
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United States of America Patent
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app pub date -
Jan 13, 2011
filing date -
Aug 29, 2008
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Abandoned
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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.
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