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

Similar works

Full text

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

This paper was published in CiteSeerX.

Having an issue?

Is data on this page outdated, violates copyrights or anything else? Report the problem now and we will take corresponding actions after reviewing your request.