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Synthesis of bis(indole)-1,2,4-triazinones - The Stoltz Group

A Facile Synthesis of Deaza-Analogues of the Bisindole Marine Alkaloid Topsentin

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10.1021/ja0558948 - American Chemical Society

Synthesis of the indenotryptoline bisindole alkaloid, BE-54017, was accomplished using osmium-promoted cis-dihydroxylation of maleimide as a key step. After optical resolution, the absolute configuration of this molecule was determined by comparing its optical rotation and HPLC profile to those obtained for BE-54017 derived from enantiopure cladoniamide A, whose stereochemistry has been reported previously. BE-54017 with the correct absolute stereochemistry induced apoptosis of epidermal growth factor (EGF)-stimulated EGF receptor overexpressing A431 cells and inhibited vacuolar-type H+-ATPase (V-ATPase).

Organic Letters (ACS Publications)

A new protocol for the synthesis of 2,2′-bisindole-3-acetic acid derivatives from aldimines derived from 2-aminocinnamic acid derivatives and indole-2-carboxaldehyde was developed via a cyanide-catalyzed imino-Stetter reaction. With this protocol, the divergent total syntheses of arcyriaflavin A, a representative indolocarbazole natural product, and calothrixin B, a representative indolo[3,2-]phenanthridine natural product, were completed using a 2,2′-bisindole-3-acetic acid derivative as the common intermediate.

Journal of Asian Natural Products Research: Vol 19, No 12

28/03/2015 · Synthesis and biological evaluation of 1,3,4-oxadiazole-linked bisindole derivatives as anticancer agents

The synthesis of iodo-substituted tetracyclic indole fused azulene derivatives was achieved from the reaction of 2-(substituted phenylethynyl)-benzaldehydes and different indoles in the presence of molecular iodine. The reaction involves the formation of a bisindole from the corresponding 2-(substituted phenylethynyl)benzaldehyde and indole followed by iodocyclization in a one-pot cascade process. A wide range of 2-(substituted phenylethynyl)-benzaldehydes and indoles were utilized in this protocol to derive a diverse range of iodo-substituted tetracyclic indole fused azulene derivatives in moderate to good yields. Further functionalizations of the iodo-substituted tetracyclic indole fused azulenes were achieved by various palladium-catalyzed crosscoupling reactions to generate highly substituted tetracyclic indole fused azulene derivatives.

AB - Synthesis of the indenotryptoline bisindole alkaloid, BE-54017, was accomplished using osmium-promoted cis-dihydroxylation of maleimide as a key step. After optical resolution, the absolute configuration of this molecule was determined by comparing its optical rotation and HPLC profile to those obtained for BE-54017 derived from enantiopure cladoniamide A, whose stereochemistry has been reported previously. BE-54017 with the correct absolute stereochemistry induced apoptosis of epidermal growth factor (EGF)-stimulated EGF receptor overexpressing A431 cells and inhibited vacuolar-type H+-ATPase (V-ATPase).

Publishes recent advances in natural products chemistry.

N2 - Synthesis of the indenotryptoline bisindole alkaloid, BE-54017, was accomplished using osmium-promoted cis-dihydroxylation of maleimide as a key step. After optical resolution, the absolute configuration of this molecule was determined by comparing its optical rotation and HPLC profile to those obtained for BE-54017 derived from enantiopure cladoniamide A, whose stereochemistry has been reported previously. BE-54017 with the correct absolute stereochemistry induced apoptosis of epidermal growth factor (EGF)-stimulated EGF receptor overexpressing A431 cells and inhibited vacuolar-type H+-ATPase (V-ATPase).

N2 - The synthesis of iodo-substituted tetracyclic indole fused azulene derivatives was achieved from the reaction of 2-(substituted phenylethynyl)-benzaldehydes and different indoles in the presence of molecular iodine. The reaction involves the formation of a bisindole from the corresponding 2-(substituted phenylethynyl)benzaldehyde and indole followed by iodocyclization in a one-pot cascade process. A wide range of 2-(substituted phenylethynyl)-benzaldehydes and indoles were utilized in this protocol to derive a diverse range of iodo-substituted tetracyclic indole fused azulene derivatives in moderate to good yields. Further functionalizations of the iodo-substituted tetracyclic indole fused azulenes were achieved by various palladium-catalyzed crosscoupling reactions to generate highly substituted tetracyclic indole fused azulene derivatives.

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  • Total synthesis of indole and dihydroindole alkaloids

    15/12/1976 · 1

  • 02/02/2016 · Downloadable

    Helv Chim Acta

  • Synthesis and assignment of the absolute configuration …

    1976 Dec 15;59(8):2858-82

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US5034320A - Vinblastine synthesis - Google Patents

Propylene carbonate (PC) is a polar aprotic substance with very similar physicochemical characteristics to the organic solvents traditionally used for organic synthesis, such as acetonitrile and acetone. Therefore, PC is beginning to be used as a “green” sustainable alternative solvent for chemical transformations. PC is a low toxicity, non-corrosive colourless liquid with a high boiling point and low vapour pressure. It is biodegradable and economical, allowing its large-scale use. PC can be prepared by a reaction between propylene epoxide and carbon dioxide with 100% atomic economy. The easy preparation of propylene epoxide and the use of an available, abundant, economical, and renewable source of carbon, such as CO2, make this process one of the best routes for the synthesis of PC. Therefore, we present in this review numerous catalytic systems that have been studied to improve the efficiency of this reaction. Certain interesting examples of reactions using PC are found in the literature, of which we discuss asymmetric hydrogenation, hydrosilylation, asymmetric aldol reactions, the asymmetric synthesis of cyanohydrins, the synthesis of heterocyclic compounds, such as bisindole and tetrahydroquinoline, the hydroacylation of alkynes, α-hydrazination reactions, oxidations, the Sonogashira reaction, allylic alkylation and asymmetric amination, the Heck reaction, enzymatic kinetic resolution, and isomerisation-hydroformylation reactions.

Stereocontrolled total synthesis of (+)-vincristine

AB - A series of novel spiro[indole-thiazolidine]spiro[indole-pyran] derivatives were synthesized from N-(bromoalkyl)indol-2,3-diones via monospiro-bisindole intermediates; the two indole nuclei being connected via N-(CH(2))(n)-N linker. Synthesized compounds were evaluated for their antimicrobial activities in vitro against three Gram-positive bacteria (Staphylococcus aureus, Bacillus subtilis, and Staphylococcus epidermis), four Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa, Salmonella typhi, and Klebsiella pneumonia) as well as four fungi (Aspergillus niger, Aspergillus fumigatus, Aspergillus flavus, and Candida albicans) using Cup plate method. Bis spiro-indoles exhibited stronger antibacterial and antifungal efficiency than their corresponding mono spiro-indoles. Compound 10e, the most active derivative was shown to inhibit the growth of all bacterial strains and two fungal strains (A. niger and C. albicans).

Thieme E-Books & E-Journals - Synthesis / …

The total synthesis of the marine bisindole alkaloid (+)-cis-dihydrohamacanthin B was achieved from optically pure (R)-indolylglycinol.

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