Organocuprate Conjugate-addition-Enolate-alkylation Reactions: A New Synthesis of 11-Deoxyprostaglandins

DOI: 10.1039/P19810001407

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 1407 - 1410 (1981)

Update date:2022-09-26

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Authors:

Dixon, Andrew J.

Taylor, Richard J. K.

Newton, Roger F.

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Article abstract of DOI:10.1039/P19810001407

A short synthesis of a key 11-deoxyprostaglandin precursor, 6β-<(E)-3-oxo-oct-1-enyl>-cis-α-2-oxabicyclo<3.3.0>octan-3-one (11), is reported.Important reactions in the synthesis include preparation of 2α-allyl-3β-<(E)-3-oct-1-enyl>cyclopentanone (4) by an organocuprate conjugate-addition-enolate-alkylation reaction, regiospecific epoxidation-cyclisation of the alcohol (7) to give 6β-<(E)-3-oct-1-enil>-3-hydroxymethyl-cis-α-2-oxabicyclo<3.3.0>octane (9), and oxidative degradation of (9) with manganese dioxide to give 6β-<(E)-3-oct-1-enyl)-cis-α-2-oxabicyclo<3.3.0>octan-3-one (10).

Full text of DOI:10.1039/P19810001407

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