What question did this study set out to answer?

Establish a reliable synthetic route for producing the tumor-inhibiting alkaloid ellipticine, 9-methoxyellipticine, and related pyrido[4,3-b]carbazole derivatives.

December 1, 1967Australian Journal of Chemistry

Synthesis of the tumour-inhibitory alkaloids, ellipticine, 9-methoxyellipticine, and related pyrido4,3-bcarbazoles

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LDLK DaltonPlant Industry SDS Demerac BEBC ElmesCSIRO Manufacturing

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Implication

Chemical synthesis study demonstrates orthophosphoric acid-catalyzed cyclization of azomethines into ellipticine derivatives, highlighting an effective route to tumor-inhibiting alkaloids.

Key Points

Establish a reliable synthetic route for producing the tumor-inhibiting alkaloid ellipticine, 9-methoxyellipticine, and related pyrido[4,3-b]carbazole derivatives.
Applied an approach based on the Cranwell and Sexton scheme using azomethines of 3-formylcarbazoles and aminoacetal.
Utilized orthophosphoric acid to mediate the ring-forming cyclization step that had previously failed under earlier conditions.
Orthophosphoric acid successfully induced cyclization of azomethine precursors into substituted 6H-pyrido[4,3-b]carbazoles.
Synthesized seven distinct analogs, including ellipticine (6,11-dimethyl-), 9-methoxyellipticine, and polymethylated, brominated, and nitrated pyrido[4,3-b]carbazole derivatives.

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Dalton et al. (1967) studied this question.

synapsesocial.com/papers/6a7a8d27684c0941cf324645 https://doi.org/10.1071/ch9672715

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Implication

Chemical synthesis study demonstrates orthophosphoric acid-catalyzed cyclization of azomethines into ellipticine derivatives, highlighting an effective route to tumor-inhibiting alkaloids.

Synthesis of the tumour-inhibitory alkaloids, ellipticine, 9-methoxyellipticine, and related pyrido4,3-bcarbazoles

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Key Points

Cite This Study

Synthesis of the tumour-inhibitory alkaloids, ellipticine, 9-methoxyellipticine, and related pyrido4,3-bcarbazoles

Discussion

Member takes

Implication

Key Points

Cite This Study

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