Photocyclisation of enamides. Part 39. General strategy for the synthesis of pseudodistomins: synthesis of triacetates of (±)-tetrahydropseudodistomin and proposed structures of pseudodistomins A and B

Naito, Takeaki; Yuumoto, Yoko; Kiguchi, Toshiko; Ninomiya, Ichiya

doi:10.1039/p19960000281

Cited by 16 publications

(6 citation statements)

References 20 publications

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“…The photocyclization with more complex heterocyclic amides has been used to contribute to structure determination of pseudodistonin A and B. 160 Figure 7.…”

Section: Photochemical Cyclizationsmentioning

confidence: 99%

Photochemical rearrangements in organic synthesis and the concept of the photon as a traceless reagent

Lefebvre

Hoffmann

2021

Nontraditional Activation Methods in Green and Sustainable Applications

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Many photochemical reactions are carried out under particular sustainable conditions. Often no chemical activation is necessary and the photon is considered as a traceless reagent. These reactions give access to unusual molecular structures and therefore are highly appreciated for application to organic synthesis, especially in heterocyclic chemistry. In this context, photochemical position isomerizations of heterocyclic compounds are discussed. Photochemical rearrangements induced by electron and hydrogen atom transfer (HAT) are also used for the preparation of heterocyclic compounds. Photochemical electrocyclization is discussed with sixmembered heterocycles such as pyridine derivatives. Finally, photochemically induced cyclization are presented as a very suitable method for the construction of heterocycles. The synthesis of biologically active compounds is particularly focused. Thus perspectives of sustainable chemistry are presented for the pharmaceutical and agrochemical industry.

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“…The photocyclization with more complex heterocyclic amides has been used to contribute to structure determination of pseudodistonin A and B. 160 Figure 7.…”

Section: Photochemical Cyclizationsmentioning

confidence: 99%

Photochemical rearrangements in organic synthesis and the concept of the photon as a traceless reagent

Lefebvre

Hoffmann

2021

Nontraditional Activation Methods in Green and Sustainable Applications

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“…Transformation of the functional groups in 25 using conventional methods led to the synthesis of acetates of (Ϯ)-pseudodistomins A and B and the tetrahydro derivatives (Chart 6). 24,25) Our first synthesis of an acetate of natural alkaloids provided concrete evidence for the structure, particularly the 6,8-diene part that was incorrectly proposed in the structure determination of natural products.…”

Section: Synthesis Of Pseudodistomin Alkaloidsmentioning

confidence: 99%

Development of New Synthetic Reactions for Nitrogen-Containing Compounds and Their Application

Naito

2008

Chem. Pharm. Bull.

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Nitrogen-containing compounds are core parts not only of natural and synthetic medicines but also of biologically active compounds including natural products. This review focuses on the development of new synthetic reactions for nitrogen-containing compounds via three methodologies: the reductive photocycloaddition reaction of enamides, radical addition reaction, and nucleophilic addition reaction. Newly developed reactions were successfully applied to the synthesis of various types of nitrogen-containing compounds including medicines, lead compounds to new drugs, natural alkaloids, and others.

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“…The pseudodistomins A 86 and B 87 were isolated 70 from the Okinawan tunicate, Pseudodistomo kanoko and are apparently the first piperidine alkaloids identified from a marine source. Total synthesis of 86 and 87 71 has established that the double bond geometry and location were incorrectly assigned in the first place. This was further confirmed after degradation analysis of fresh compound from a source.…”

Section: Pyridone and Hydropyridone Alkaloidsmentioning

confidence: 99%

Pyrrole, pyrrolidine pyridine, piperidine, azepine and tropane alkaloids

O’Hagan¹

1997

Nat. Prod. Rep.

228

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Photocyclisation of enamides. Part 39. General strategy for the synthesis of pseudodistomins: synthesis of triacetates of (±)-tetrahydropseudodistomin and proposed structures of pseudodistomins A and B

Cited by 16 publications

References 20 publications

Photochemical rearrangements in organic synthesis and the concept of the photon as a traceless reagent

Photochemical rearrangements in organic synthesis and the concept of the photon as a traceless reagent

Development of New Synthetic Reactions for Nitrogen-Containing Compounds and Their Application

Pyrrole, pyrrolidine pyridine, piperidine, azepine and tropane alkaloids

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