Facile Synthesis of Spirocyclic Lactams via [3+2] and [3+3] Aza‐Annulation Reactions

Hayrapetyan, Davit; Stepanova, V. N.

doi:10.1002/ejoc.202100255

Cited by 3 publications

(1 citation statement)

References 52 publications

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“…Initially, advanced intermediate 46a was subjected to sequential cleavage of the TES (TBAF, AcOH) and PMB (DDQ, CH 2 Cl 2 /MeOH) protecting groups, which subsequently led to spontaneous ring closures, respectively, to form rings BCDE as depicted in structure 47 (39% overall yield from 46a , 1:3 dr at C16 with the desired product being the minor component). The absolute configuration of the two isomers ( 47 and C16- epi - 47 ) were confirmed by NOE spectroscopic studies (cf. regions A, B, and C, see details in Table ).…”

Section: Resultsmentioning

confidence: 99%

A Highly Convergent Total Synthesis of Norhalichondrin B

et al. 2021

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A new synthetic strategy for the total synthesis of norhalichondrin B featuring a highly convergent approach and our recently disclosed reverse approach for the synthesis of cyclic ether structural motifs is disclosed. Resulting in the shortest route to norhalichondrin B disclosed thus far, the reported total synthesis was achieved through the synthesis of two almost equally complex fragments whose coupling and short elaboration sequence featured an essential epimerization of the C16 stereocenter occurring concurrently with a simple acid-induced deprotection, a tactic based on a prior study along the synthetic route. This unprecedented strategy within the halichondrin family of natural products could find practical application to the synthesis of other more or less complex natural or designed halichondrin analogues.

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Section: Resultsmentioning

confidence: 99%

A Highly Convergent Total Synthesis of Norhalichondrin B

et al. 2021

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One‐Step Nickel‐Catalyzed Synthesis of Alpha‐Arylidene and Gamma Hydroxy‐Substituted N‐Methyl‐2‐Pyrrolidones

Sirvin Rajan,

Mok,

Lee

et al. 2024

Asian J Org Chem

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This study describes a method to synthesize compounds with an arylidene group at the alpha position of N‐methyl‐2‐pyrrolidone (NMP) and an alcohol group at the gamma position in a single‐step reaction using NMP and an aldehyde. The highest yields were obtained with Ni(glyme)Cl2 as a nickel catalyst and tert‐butyl hydroperoxide as the oxidant, and various aryl aldehydes reacted under optimal conditions to yield the target compounds.

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Decarboxylation of Aza-Annulation Products as a Synthetic Route to 3-Pyrrolin-2-ones and 1,2,3,4-Tetrahydropyridin-2-ones

Petrova,

Kaipov,

Yussupova

et al. 2024

J. Org. Chem.

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Aza-annulation of enamines derived from βketoesters with maleic and itaconic anhydrides proceeds with excellent diastereoselectivity to provide functionalized γand δlactams. Further hydrolysis of the aza-annulation products resulted in dicarboxylic acids that underwent spontaneous decarboxylation under ambient conditions. The decarboxylation of β−γ unsaturated carboxylic acids with an electron-rich enamide C�C bond proceeds with the migration of the C�C bond and serves as a practical synthetic entry into 3-pyrrolin-2-ones and 1,2,3,4tetrahydropyridin-2-ones.

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Facile Synthesis of Spirocyclic Lactams via [3+2] and [3+3] Aza‐Annulation Reactions

Cited by 3 publications

References 52 publications

A Highly Convergent Total Synthesis of Norhalichondrin B

A Highly Convergent Total Synthesis of Norhalichondrin B

One‐Step Nickel‐Catalyzed Synthesis of Alpha‐Arylidene and Gamma Hydroxy‐Substituted N‐Methyl‐2‐Pyrrolidones

Decarboxylation of Aza-Annulation Products as a Synthetic Route to 3-Pyrrolin-2-ones and 1,2,3,4-Tetrahydropyridin-2-ones

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