Straightforward four-component access to spiroindolines

Kaı̈m, Laurent El; Grimaud, Laurence; Goff, X. Le; Menes‐Arzate, Martha; Miranda, Luis D.

doi:10.1039/c1cc12236c

Cited by 53 publications

(18 citation statements)

References 59 publications

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“…In a 10 mmol scale reaction, the yield could be further improved to 80 %. As a comparison, other catalysts such as Mn(acac) 3 and Cu(OAc) 2 13 gave a lower yield (entries 8 and 9), whereas CeCl 3 14 did not promote the reaction at all (entry 10).…”

Section: Methodsmentioning

confidence: 96%

Total Synthesis of Indole Alkaloid Alsmaphorazine D

Zhu¹,

Liu²,

Chen³

et al. 2014

Angewandte Chemie

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A concise total synthesis of rac‐alsmaphorazine D has been described for the first time. The efficient synthetic strategy features four key transformations: 1) a catalytic intramolecular oxidative cyclization for the δ‐lactamindole backbone; 2) an oxidative cyclic aminal formation for the hexahydropyrrolo[2,3‐b]pyrrole framework; 3) a transannular radical cyclization for the construction of the diazabicyclo[3.3.1]nonane structure; and 4) a one‐pot desilylation/double epimerization reaction that affirms the relative stereochemistry.

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Section: Methodsmentioning

confidence: 96%

Total Synthesis of Indole Alkaloid Alsmaphorazine D

Zhu¹,

Liu²,

Chen³

et al. 2014

Angewandte Chemie

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show abstract

“…[32][33][34] To access such alkaloids in a one pot cascade fashion and securing diversity is highly desirable from the viewpoint of sustainable chemistry. The first one-pot multicomponent attempt towards such complex alkaloids was reported by El Kaïm and co-workers 32 whereby spirocyclization was achieved using a stoichiometric amount of Cu(II) salt in refluxing DBU-THF system.…”

Section: View Article Onlinementioning

confidence: 99%

Metal-mediated post-Ugi transformations for the construction of diverse heterocyclic scaffolds

et al. 2015

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The Ugi-4CR is by far one of the most successful multicomponent reactions leading to high structural diversity and molecular complexity. However, the reaction mostly affords a linear peptide backbone, enabling post-Ugi transformations as the only solution to rigidify the Ugi-adduct into more drug like species. Not surprisingly, the development of these transformations, leading to new structural frameworks, has expanded rapidly over the last few years. As expected, palladium-catalyzed reactions have received the foremost attention, yet other metals, particularly gold complexes, are fast catching up. This tutorial review outlines the developments achieved in the past decade, highlighting the modifications that are performed in a sequential or domino fashion with emphasis on major concepts, synthetic applications of the derived products as well as mechanistic aspects.

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“…In a 10 mmol scale reaction, the yield could be further improved to 80 %. As a comparison, other catalysts such as Mn(acac) 3 and Cu(OAc) 2 [13] gave a lower yield (entries 8 and 9), whereas CeCl 3 [14] did not promote the reaction at all (entry 10). Encouraged by the facile construction of 6, we turned our attention to building up the hexahydropyrrolo[2,3-b]pyrrole fused diazabicyclo[3.3.1]nonane skeleton (Scheme 2).…”

mentioning

confidence: 99%

Total Synthesis of Indole Alkaloid Alsmaphorazine D

et al. 2014

View full text Add to dashboard Cite

A concise total synthesis of rac-alsmaphorazine D has been described for the first time. The efficient synthetic strategy features four key transformations: 1) a catalytic intramolecular oxidative cyclization for the δ-lactamindole backbone; 2) an oxidative cyclic aminal formation for the hexahydropyrrolo[2,3-b]pyrrole framework; 3) a transannular radical cyclization for the construction of the diazabicyclo[3.3.1]nonane structure; and 4) a one-pot desilylation/double epimerization reaction that affirms the relative stereochemistry.

show abstract

Straightforward four-component access to spiroindolines

Cited by 53 publications

References 59 publications

Total Synthesis of Indole Alkaloid Alsmaphorazine D

Total Synthesis of Indole Alkaloid Alsmaphorazine D

Metal-mediated post-Ugi transformations for the construction of diverse heterocyclic scaffolds

Total Synthesis of Indole Alkaloid Alsmaphorazine D

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