A simple biomimetic synthesis of styelsamine B.

  title={A simple biomimetic synthesis of styelsamine B.},
  author={David A. Skyler and Clayton H. Heathcock},
  journal={Organic letters},
  volume={3 26},
An extremely rapid, low cost, and environmentally friendly entry into the pyridoacridine family of alkaloids has been devised, as demonstrated here by the first total synthesis of styelsamine B (3) and its oxidation to the quinoneimine cystodytin J (4). The known reaction of cystodytin J with methanethiol makes this a formal synthesis of diplamine. [reaction: see text] 

Topics from this paper

Synthetic ventures inspired by biosynthetic hypotheses: the evolution of a method for the oxidative amidation of phenols
We describe the development of a technique for the oxidative conversion of 4-alkyl phenols to derivatives of the corresponding 4-alkyl-4-amino-2,5-cyclohexanediones. This transformation, which wasExpand
Biomimetic Cationic Cyclization toward ent-Kaurene-type Diterpenoids
Terpenoids comprise the largest family of natural products and include various structurally different genus which play important roles in living organisms. Biosynthetically, diterpenoids are derivedExpand
Oxidative Cyclization of Kynuramine and Ynones Enabling Collective Syntheses of Pyridoacridine Alkaloids.
  • Dongfang Jiang, Shaozhong Wang
  • Medicine
  • The Journal of organic chemistry
  • 2021
A cerium(III)-catalyzed oxidative cyclization of kynuramine and ynones has been reported as a key reaction in the total synthesis of marine pentacyclic pyridoacridine alkaloids featuring differentExpand
Formation of the dimethylbenzimidazole ligand of coenzyme B(12) under physiological conditions by a facile oxidative cascade.
Dimethylbezimidazole, the axial ligand of vitamin B(12), is synthesized from riboflavin by a two-electron oxidation, a retro-aldol condensation, and a second two-electron oxidation. This oxidativeExpand
Marine pyridoacridine alkaloids and synthetic analogues as antitumor agents
The pyridoacridines have not a sole mode of action, but it seems that the reductive DNA cleavage mediated by reactive oxygen species is a potential general mode ofaction. Expand
Structural Revision of Pseudocerosine and Validation of a Biosynthetic Proposal for E-ring Formation in Pyridoacridine Alkaloids.
This study validates a biosynthesis proposal for E-ring formation in this revered class of alkaloids, and pseudocerosine (along with its intermediates described herein) is a new branch on the pyridoacridine family tree. Expand
New Perspectives in the Chemistry of Marine Pyridoacridine Alkaloids †
This review summarizes the progress in the chemistry of pyridoacridine alkaloids that was made in the last one-and-a-half decades. Expand
Oxidative cascades: a facile biosynthetic strategy for the assembly of complex molecules.
This review will describe the application of the two-electron oxidation/aromatization motif to the synthesis of dimethylbenzimidazole, pyoverdine, actinomycin, cystodytin, pyrroloquinoline quinone, and the cataract pigment. Expand
Bioinspired Syntheses of the Pyridoacridine Marine Alkaloids Demethyldeoxyamphimedine, Deoxyamphimedine, and Amphimedine.
The versatility of the method was demonstrated by the synthesis of non-natural ethyl and benzyl congeners of deoxyamphimedine and amphimedines. Expand
Isolation, Synthesis and Medicinal Significance of Marine Pyridoacridine Alkaloids
Pyridoacridine alkaloids, distributed in marine organisms have emerged as an important class of compounds due to their uniqure chemical architecture, diversity and medicinal significance. TheseExpand


Total synthesis of cystodytin J, diplamine and shermilamine B
Abstract Concise, efficient total syntheses of three cytotoxic marine alkaloids are described. Key phases of the synthesis are a useful pyridine-forming reaction and a triplet-sensitizedExpand
A two step biomimetic total synthesis of eilatin
Abstract The symmetrical tetraaza heptacyclic alkaloid eilatin ( 1 ) was synthesized in a biomimetic two step reaction from catechol and monotrifluoro kynuramine ( 6 ) under oxidative conditions inExpand
Biomimetic Synthesis of Ascididemin and Derivatives
A two-step biomimetic synthesis of the pentacyclic pyrido[2,3,4-kl]acridine marine alkaloid ascididemin (3a) from quinolinequinone 5a and N-trifluoroacetamidokynuramine (4) is described. The crucialExpand
Total Synthesis of Diplamine, a Cytotoxic Pyridoacridine Alkaloid from a Pacific Tunicate
The total synthesis of diplamine (1) has been accomplished in 21 steps from commercially available materials
Biomimetic Synthesis of Pyrido(2,3,4-kl)acridines.
Abstract A short new biomimetic route to the pyrido[2,3,4- kl ]acridine ring system has been developed from readily available benzoquinone, or hydroquinone precursors, and β,β′-diaminoketones likeExpand
The biomimetic synthesis of marine alkaloid related pyrido- and pyrrolo[2,3,4-kl]acridines
Abstract A biomimetic reaction between β,β′-diamenoketones (e.g. kynuramine, kynurenine or o,o′-diaminobenzophenone) and a variety cyclohexanediones and quinones leading to pyrido[2,3,4-kl) acridinesExpand
Inhibition of topoisomerase II catalytic activity by pyridoacridine alkaloids from a Cystodytes sp. ascidian: a mechanism for the apparent intercalator-induced inhibition of topoisomerase II.
The results suggest that disruption of the function of TOPO II, subsequent to intercalation, is a probable mechanism by which pyridoacridines inhibit the proliferation of HCT cells. Expand