Synthesis of Arnoamine B and Related Compounds

Nakahara, Shinsuke; Kubo, Akinori; Mikami, Yuzuru; Mitani, Hiroki

doi:10.3987/com-07-11074

Cited by 9 publications

(7 citation statements)

References 6 publications

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“…Work employing this final step also led to arnoamine B itself. [65,66] Scheme 31. Synthesis of arnoamine A skeleton from an indole.…”

Section: Synthesesmentioning

confidence: 99%

“…Synthesis of arnoamine A skeleton from an indole. [65,66] The Authors' synthesis of ascididemine began with the acridone 105 (Scheme 32) [67] converted as shown into ethynylacridine 106. The next step was entirely novel involving reaction with sodium diformylamide and producing the "top" pyridine ring directly 107.…”

Section: Synthesesmentioning

confidence: 99%

“…Formation of the final bond relied on an intramolecular radical substitution. Work employing this final step also led to arnoamine B itself , …”

Section: Pyrido[234‐kl]acridinementioning

confidence: 99%

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Pyridoacridines in the 21st Century

Joule

Álvarez

2019

Eur J Org Chem

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This minireview summarizes the work developed during this century with compounds containing the pyridoacridine scaffold in its different isomeric forms. The isolation of natural products, syntheses, bioactivities, chelation capacity, and other properties of compounds containing this framework are discussed. For reasons of length, only compounds containing a maximum of seven condensed rings have been considered, with a few exceptions.

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“…Work employing this final step also led to arnoamine B itself. [65,66] Scheme 31. Synthesis of arnoamine A skeleton from an indole.…”

Section: Synthesesmentioning

confidence: 99%

Section: Synthesesmentioning

confidence: 99%

See 1 more Smart Citation

Pyridoacridines in the 21st Century

Joule

Álvarez

2019

Eur J Org Chem

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“…A related approach to arnoamine B ( 185 ) was reported by Nakahara et al in 2007 [ 53 ]. Starting from readily available 5-nitroquinoline 167 (see Scheme 25 ), alkaloid 185 was prepared in four steps with an overall yield of 12%.…”

Section: Arnoamine-type Pyridoacridinesmentioning

confidence: 99%

“…Despite the low yield, this protocol is more convenient than Delfourne’s protocol starting from the des-methyl compound 188 and utilizing a Fischer synthesis for construction of the pyrrole ring. Finally, cyclization to arnoamine B ( 185 ) was accomplished in 81% yield under intramolecular N -arylation of the pyrrole moiety of 191 under palladium(II) acetate catalysis ( Scheme 27 ) [ 53 ].…”

Section: Arnoamine-type Pyridoacridinesmentioning

confidence: 99%

New Perspectives in the Chemistry of Marine Pyridoacridine Alkaloids

Plodek

Bracher

2016

Marine Drugs

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Secondary metabolites from marine organisms are a rich source of novel leads for drug development. Among these natural products, polycyclic aromatic alkaloids of the pyridoacridine type have attracted the highest attention as lead compounds for the development of novel anti-cancer and anti-infective drugs. Numerous sophisticated total syntheses of pyridoacridine alkaloids have been worked out, and many of them have also been extended to the synthesis of libraries of analogues of the alkaloids. This review summarizes the progress in the chemistry of pyridoacridine alkaloids that was made in the last one-and-a-half decades.

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Leimgruber–Batcho Indole Synthesis

Gribble

2016

Indole Ring Synthesis

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Synthesis of Arnoamine B and Related Compounds

Cited by 9 publications

References 6 publications

Pyridoacridines in the 21st Century

Pyridoacridines in the 21st Century

New Perspectives in the Chemistry of Marine Pyridoacridine Alkaloids

Leimgruber–Batcho Indole Synthesis

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