- Prostanoids: Synthesis of enantiomers of 15-deoxy-16-hydroxy-16-methylprostaglandin E1
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Four optically pure isomers of methyl 11,16-dihydroxy-16-methyl-9-oxoprost-13-enoate (1a-1d) were synthesized using an approach reverse to the classical Corey procedure, the key intermediates being the easily accessible (-)- and (+)-enantiomers of the Corey lactone, 2a and 2b.
- Terinek, Miroslav,Kozmik, Vaclav,Palecek, Jaroslav
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p. 1325 - 1341
(2007/10/03)
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- Cyclopenteneheptenoic acid derivatives and method of preparation thereof
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This invention relates to a novel cyclopenteneheptenoic acid derivative having the following formula STR1 wherein R1 is hydrogen, --COCH3, --COCF3, --CO--phenyl, or a hydroxyl protecting group such as tetrahydropyranyl, tetrahydrofuranyl, or tri-lower alkylsilyl; wherein R2 is --CH2 OR1, --COOH, --COOR, --CHO, --CH2 --OSi(R12)3, STR2 wherein R is lower alkyl and each R12 is independently lower alkyl or aryl; and wherein Y is ethylene, cis-vinylene, trans-vinylene, or acetylene. Also disclosed is a novel process for preparation of the above-defined cyclopenteneheptenoic acid derivative. This process involves coupling of a higher order cuprate complex with a chiral cyclopentene compound. The resultant product is particularly useful as a starting compound for high yield synthesis of optically active prostaglandins.
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