Triply-convergent synthesis of a homochiral 3,3-dimethyl, 15-cyclohexyl prostacyclin analog

Allylic bromocuprate reagent 13b undergoes synfacial SN2′ addition to homochiral allyl ammonium salt 14 to provide vinyl sulfone 15 as a single stereoisomer. Addition of homochiral acetylenic anion 18 to vinyl sulfone 17 smoothly provides the bicyclic sulfone 19 which is further transformed to prost...

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Published inBioorganic & medicinal chemistry letters Vol. 1; no. 11; pp. 649 - 652
Main Authors Berglund, R.A., Braish, T.F., Jakubowski, J.A., Fuchs, P.L.
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 1991
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Summary:Allylic bromocuprate reagent 13b undergoes synfacial SN2′ addition to homochiral allyl ammonium salt 14 to provide vinyl sulfone 15 as a single stereoisomer. Addition of homochiral acetylenic anion 18 to vinyl sulfone 17 smoothly provides the bicyclic sulfone 19 which is further transformed to prostacyclin analog 22 . Analog 22 was only a weak inhibitor of platelet aggregation having an IC 50 of 0.48 μM. Graphic
ISSN:0960-894X
1464-3405
DOI:10.1016/S0960-894X(01)81170-7