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Prostanoids: LXXVII. Synthetic Approaches to Sterically Overcrowded Cyclopentenones

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Abstract

Condensation of (±)-5-allyl-2,3,5-trichloro-4,4-dimethoxy-2-cyclopentenone with phenylethynylmagnesium bromide in THF gave (±)-5α-allyl-2,3,5β-trichloro-4,4-dimethoxy-1α-phenylethynyl-2-cyclopenten-1β-ol which chemoselectively reacted with ozone at the terminal double bond, affording (±)-2,3,5β-trichloro-5α-formylmethyl-4,4-dimethoxy-1α-phenylethynyl-2-cyclopenten-1β-ol. Oxidation of the latter with H2CrO4 yielded a mixture of the expected product, (±)-5α-carboxymethyl-2,3,5β-trichloro-4,4-dimethoxy-1α-phenylethynyl-2-cyclopenten-1β-ol, and anomalous profound oxidation product, (±)-2,3,5β-trichloro-5α-carboxymethyl-4,4-dimethoxy-1α-(2-oxo-2-phenylacetyl)-2-cyclopenten-1β-ol. Attempts to remove protective methoxy groups in these compounds under standard conditions were unsuccessful.

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  1. Ufa Research Center, Russian Academy of Sciences, Institute of Organic Chemistry, pr. Oktyabrya 71, Ufa, 450054, Bashkortostan, Russia

    F. A. Akbutina, S. A. Torosyan & M. S. Miftakhov

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  1. F. A. Akbutina
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  2. S. A. Torosyan
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  3. M. S. Miftakhov
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Akbutina, F.A., Torosyan, S.A. & Miftakhov, M.S. Prostanoids: LXXVII. Synthetic Approaches to Sterically Overcrowded Cyclopentenones. Russian Journal of Organic Chemistry 37, 356–358 (2001). https://doi.org/10.1023/A:1012324306438

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  • DOI: https://doi.org/10.1023/A:1012324306438

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