The Bisindole Alkaloids

Cordell, Geoffrey A.

doi:10.1002/9780470186954.ch11

Cited by 9 publications

(3 citation statements)

References 259 publications

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“…In the case of the plant monoterpenoid indole alkaloids, most of the enantiomeric metabolites occur in different species as a single enantiomer and only sometimes as a racemic mixture. Examples include (+)-, (−)-, (±)-vincadifformine; (+)-, (−)-, (±)-vincamine; (+)-, (−)-, (±)-eburnamonine; and (+)-catharanthine and (−)-coronaridine, the latter exemplifying the case of alkaloids that are not strictly enantiomers but belong to opposite antipodal series (enantiomeric congeners or enantiodivergent congeners). − One group of the monoterpenoid indole alkaloids characterized by the occurrence of enantiomeric pairs is the eburnane group of alkaloids, where for a number of these alkaloids both enantiomers are known [e.g., (+)- and (−)-eburnamonine, 1 and 9 , respectively] and a single enantiomer is usually found in a particular species [e.g., (−)-eburnamine 2 in Kopsia larutensis , (+)-eburnamine 10 in K. jasminiflora ] and where to date racemic or scalemic mixtures are rarely encountered . In our extensive studies of the Malaysian Kopsia (and Leuconotis ), where a significant number of eburnane alkaloids were isolated, we have observed the occurrence of biosynthetic enantiodivergence and herein report our results.…”

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Biosynthetic Enantiodivergence in the Eburnane Alkaloids from Kopsia

et al. 2017

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Reexamination of the absolute configuration of recently isolated eburnane alkaloids from Malaysian Kopsia and Leuconotis species by X-ray diffraction analysis and ECD/TDDFT has revealed the existence of biosynthetic enantiodivergence. Three different scenarios are discerned with respect to the composition of the enantiomeric eburnane alkaloids in these plants: first, where the new eburnane congeners possess the same C-20, C-21 absolute configurations as the common eburnane alkaloids (eburnamonine, eburnamine, isoeburnamine, eburnamenine) occurring in the same plant; second, where the new eburnane congeners possess opposite or enantiomeric C-20, C-21 absolute configurations compared to the common eburnane alkaloids found in the same plant; and, third, where the four common eburnane alkaloids were isolated as racemic or scalemic mixtures, while the new eburnane congeners were isolated as pure enantiomers with a common C-20, C-21 configuration (20α, 21α). Additionally, the same Kopsia species (K. pauciflora) found in two different geographical locations (Peninsular Malaysia and Malaysian Borneo) showed different patterns in the composition of the enantiomeric eburnane alkaloids. Revision of the absolute configurations of a number of new eburnane congeners (previously assigned based on the assumption of a common biogenetic origin to that of the known eburnane alkaloids co-occurring in the same plant) is required based on the present results.

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Biosynthetic Enantiodivergence in the Eburnane Alkaloids from Kopsia

et al. 2017

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“…The activity and structures of bisindole alkaloids have been reviewed and the number of isolated bisindole alkaloids are increasing [16,17,18,19]. This review is focused on the partial and total synthesis of bisindoles, as well as some dimeric indole alkaloids wherein at least one of the following monomeric units contains, as its obligate constituent, the sarpagine, macroline, ajmaline, vobasine, or pleiocarpamine systems.…”

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Synthesis of Bisindole Alkaloids from the Apocynaceae Which Contain a Macroline or Sarpagine Unit: A Review

2016

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Bisindole natural products consist of two monomeric indole alkaloid units as their obligate constituents. Bisindoles are more potent with respect to their biological activity than their corresponding monomeric units. In addition, the synthesis of bisindoles are far more challenging than the synthesis of monomeric indole alkaloids. Herein is reviewed the enantiospecific total and partial synthesis of bisindole alkaloids isolated primarily from the Alstonia genus of the Apocynaceae family. The monomeric units belong to the sarpagine, ajmaline, macroline, vobasine, and pleiocarpamine series. An up-to-date discussion of their isolation, characterization, biological activity as well as approaches to their partial and total synthesis by means of both synthetic and biosynthetic strategies are presented.

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“…3), which contain an octahydro-3a,3a′-bispyrrolo[2,3-b]indole subunit (Fig. 3, core structure 24) with vicinal all-carbon quaternary stereogenic centers, exhibit important biological activities [13] and have therefore led to a great demand for enatioselective and efficient synthetic …”

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Organocatalytic asymmetric synthesis of chiral nitrogenous heterocycles and natural products

Chen

Gong

2014

Pure and Applied Chemistry

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Nitrogen-containing chiral heterocycles represent important structural elements with wide occurrence in natural and unnatural compounds exhibiting important biological activities. Herein, we describe our recent endeavors directed toward the Brønsted acid-catalyzed 1,3-dipolar cycloaddition and alkylation reactions, together with the metal/Brønsted acid relay catalytic cascade reactions to access some typical nitrogenous heterocyclic structures and natural alkaloids, including (+)-folicanthine and (+)-gliocladin C.

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The Bisindole Alkaloids

Cited by 9 publications

References 259 publications

Biosynthetic Enantiodivergence in the Eburnane Alkaloids from Kopsia

Biosynthetic Enantiodivergence in the Eburnane Alkaloids from Kopsia

Synthesis of Bisindole Alkaloids from the Apocynaceae Which Contain a Macroline or Sarpagine Unit: A Review

Organocatalytic asymmetric synthesis of chiral nitrogenous heterocycles and natural products

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