La borrerine: Nouvel alcaloïde isolé du Borreria verticillata

Pousset, Jean-Louis; Kerharo, J; Maynart, G.; Monseur, X.; Cavé, André; Goutarel, R

doi:10.1016/0031-9422(73)85148-9

Cited by 30 publications

(19 citation statements)

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“…In the 1970s, borrerine and the bis‐indole alkaloid borreverine were isolated from the aerial parts of Borreria verticillata . Subsequently, isoborreverine and various borreverine analogue alkaloids were isolated from Flindersia fournieri along with borrerine and borreverine .…”

Section: Introductionmentioning

confidence: 99%

Biomimetic Synthesis and Studies Toward Enantioselective Synthesis of Flindersial Alkaloids

et al. 2013

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A strategy allowing both stereocontrol and control over structural isomer formation has been defined for the antimalarial flindersial alkaloids. The recently reported flinderoles were demonstrated to be derived from the natural product borrerine. The structural isomers of flinderoles, the borreverines, were also produced in vitro along with the flinderoles through the dimerization of borrerine in acidic conditions. This result is thought to replicate the biosynthesis of these compounds. Flinderoles A, B, and C, desmethylflinderole C, isoborreverine, and dimethylisoborreverine can each be synthesized in three steps from tryptamine. Furthermore, progress toward a concise enantioselective synthesis of flinderoles A, B, and C is described. This work includes enantioselective conjugate addition to an unprotected indole-appended enone.

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Section: Introductionmentioning

confidence: 99%

Biomimetic Synthesis and Studies Toward Enantioselective Synthesis of Flindersial Alkaloids

et al. 2013

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“…Borreverine (5), which was isolated from the genus Borreria in the 1970s, 5 contains a similar core, but with a different indole connectivity that translates to a cyclohexenyl/cyclopentane core. 4 These compounds differ structurally from the flinderoles, since they contain a fused cyclohexenyl/pyrrolidine core.…”

Section: The Borreverinesmentioning

confidence: 99%

Syntheses of the Bisindole Alkaloids of the Genera Borreria and Flindersia

May

2014

Strategies and Tactics in Organic Synthesis

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“…(±)-Borrerine (158), (±)-borreverine (18), and (±)-isoborreverine (17) (Scheme 5.25) were originally isolated in 1973 from Borreria verticillata, a plant used in traditional medicine of West Africa for the treatment of skin diseases [50]. Subsequently, in 1991, these natural products were re-isolated from Flindersia fournieri, a plant from New Caledonia (West Pacific) [51a].…”

Section: (±)-Borreverine and (±)-Isoborreverinementioning

confidence: 99%