oaioai:CiteSeerX.psu:10.1.1.575.3984

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Abstract

and subsequent iodine-promoted rearrangement to 2 olefins or unsymmetrical acetylenes are reported. Mixed dialkylboranes are also examined in this olefin-acetylene cross process. Significant amounts of thexyl-migrated acetylenic by-products are observed in several instances. The synthesis of either E- or 2-1,2-disubstituted olefins by roaction of boronic esters with both ( E)- and (2)-alkenyllithium reagents is examined. This study demonstrates that 50-70 % yields of either E- or 2-1,2-disubstituted olefins are obtainable from the aforementioned reagents. The overall objectives in this investigation are to assess the potential of employing organoborane intermediates in the coupling of the C13-C20 prostaglandin olefinic side chain to cyclopentenoid precursors. As part of our program directed toward the total synthesis of prostaglandin hormones we recently reported a general stereospecific approach to the synthesis of cis-2-alkyl-2-cy-clopentene-1,4-diols (1) via the three-step sequence illustrated below.2 This expeditious synthetic scheme readily affords

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oaioai:CiteSeerX.psu:10.1.1.575.3984Last time updated on 10/29/2017

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