flinderole-b and borreverine

flinderole-b has been researched along with borreverine* in 2 studies

Other Studies

2 other study(ies) available for flinderole-b and borreverine

ArticleYear
Remarkable switch of regioselectivity in Diels-Alder reaction: divergent total synthesis of borreverine, caulindoles, and flinderoles.
    Organic letters, 2014, May-16, Volume: 16, Issue:10

    Switchable reaction patterns of dimerization of indole substituted butadienes via a Lewis acid and thermal activation are reported. While under acidic conditions dimerization occurred around the internal double bond of the dienophile, a complete switch of regioselectivity was observed under thermal conditions, where dimerization occurred around the terminal double bond of the dienophile. This switch of regioselectivity was further exploited for the divergent total synthesis of structurally diverse indole alkaloid natural products.

    Topics: Alkaloids; Biological Products; Butadienes; Cycloaddition Reaction; Dimerization; Indole Alkaloids; Indoles; Molecular Structure; Stereoisomerism

2014
Biomimetic total syntheses of borreverine and flinderole alkaloids.
    The Journal of organic chemistry, 2013, Oct-18, Volume: 78, Issue:20

    Dimeric indole alkaloids represent a structurally unique class of natural products having interesting biological activities. Recently, we reported the first total synthesis of flinderoles B and C, structurally unique and potent antimalarial natural products. Central to the design of the approach and by virtue of a one-pot, acid-catalyzed dimerization reaction, the route also provided total synthesis of the borreverine class of natural products. This full account details the progress of efforts that culminated in the protecting-group-free, six-step total synthesis of all of the flindersia alkaloids: dimethylisoborreverine, isoborreverine, flinderoles A-C, and their analogues. A biomimetic approach featuring a scalable and catalytic formal [3 + 2] cycloaddition and Diels-Alder reaction is outlined in detail. On the basis of the experimental observations, a detailed mechanism has been proposed for the dimerization of tertiary alcohol 28.

    Topics: Alkaloids; Antimalarials; Biological Products; Biomimetics; Cycloaddition Reaction; Dimerization; Indole Alkaloids; Indoles; Stereoisomerism

2013