Cyclopenteneheptenoic acid derivatives and method of...

C - Chemistry – Metallurgy – 07 – C

Patent

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260/491, 260/353

C07C 69/732 (2006.01) C07C 43/315 (2006.01) C07D 303/40 (2006.01) C07D 309/10 (2006.01) C07D 309/12 (2006.01) C07D 317/20 (2006.01) C07D 493/08 (2006.01)

Patent

CA 2000179

This invention relates to a novel cyclopenteneheptenoic acid derivative having the following formula (see formula I) wherein R1 is hydrogen, -COCH3, -COCF3, -CO-phenyl, or a hydroxyl protecting group such as tetrahydropyranyl, tetrahydrofuranyl, or tri-lower alkylsilyl; wherein R2 is -CH2OR1, -COOH, -COOR, -CHO, -CH2-OSi(R12)3, (see formula II), (see formula III), (see formula IV), or (see formula V) 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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