Cycloaddition−Rearrangement Sequence of 2-Amido Substituted Furans as a Method of Synthesizing Hexahydroindolinones

Padwa, Albert; Brodney, Michael A.; Satake, Kyosuke; Straub, Christopher

doi:10.1021/jo982061+

Cited by 56 publications

(42 citation statements)

References 40 publications

(49 reference statements)

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“…[4+2] cycloaddition of 2‐amido substituted furans has been used for the synthesis of variety of substituted hexahydroindolinones . The intramolecular [4+2] aminofuran cycloaddition reaction was investigated by the study of thermal behaviour of N‐alkenylfuranylcarbamates (1) containing an unactivated π‐bond ( Scheme ) .…”

Section: Cycloaddition Reactions As a Main Tool For Developing Sustaimentioning

confidence: 99%

Aluminum‐Based Catalysts for Cycloaddition Reactions: Moving One Step Ahead in Sustainability

Dogra

Gupta

2019

ChemistrySelect

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A large variety of dienes and alkenes can be derived from plants and used further for the production of fine chemicals or biologically active compounds. Herein, we have identified such dienes/alkenes, as well as their synthetic analogues, and presented a strategy for their conversion by atom-economical cycloaddition reactions. The catalyst used for these conversions is derived from abundantly-available aluminum metal in earth's crust, which has low toxicity, easy availability and low price in comparison to the transition metals. Astonishingly, the applications of aluminum-based catalysts are underdeveloped in comparison to the d-block metal analogues. Therefore, this review summarizes the developments in the field of cycloaddition reactions by using aluminum-based catalysts, a pathway that can be pursued for developing "Sustainable Processes". . Zeolite (81) catalysed cycloaddition of isoprene with dienes 38 (a-d) Scheme 22. Synthesis of TCPD by oligomerization of DCPD and DCPD oligomer isomerisationReviews

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Section: Cycloaddition Reactions As a Main Tool For Developing Sustaimentioning

confidence: 99%

Aluminum‐Based Catalysts for Cycloaddition Reactions: Moving One Step Ahead in Sustainability

Dogra

Gupta

2019

ChemistrySelect

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“…Our synthetic strategy was to take advantage of an intramolecular Diels-Alder of an alkenyl-substituted furanyl carbamate derivative (IMDAF) [60,61]. In our approach to the core hexahydroindoline skeleton of this family of natural products, we examined the ringopening reaction of an aza-substituted oxabicyclo[2.2.1]heptene derivative.…”

Section: [4+2]-cycloaddition Chemistry Of Furanyl Carbamatesmentioning

confidence: 99%

Tandem Methodology for Heterocyclic Synthesis

Padwa

2005

ChemInform

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Tandem methodology for heterocyclic synthesis represents a powerful approach for the rapid buildup of molecular complexity from potentially simple starting materials. Work from our laboratory has shown that the rhodium(II)-catalyzed cyclization cascade of α-diazo imides represents an effective method for the synthesis of a variety of heterocyclic systems. As an extension of these studies, we became interested in using a linked Pummerer/N-acyliminium ion cyclization sequence since we felt that this combination offers unique opportunities for the assemblage of complex target molecules. A synthetic method that combines transformations of different reaction types significantly broadens the scope of such procedures in synthetic chemistry. α-Thiocarbocations generated from the Pummerer reaction of β-phenylsulfinylmethyl-α,β-unsaturated amides can be intercepted by the adjacent amido group to produce transient amino-substituted furans which undergo subsequent Diels-Alder cycloadditions. Using this domino amido Pummerer/Diels-Alder cascade, we were able to assemble novel polycyclic systems in a single operation. The key step in the process involves the generation of a reactive N-acyliminium ion by fragmentation of an amino-substituted [4+2]-cycloadduct. The successful synthesis of a number of alkaloids by this sequence of reactions reveals the usefulness and importance of this unique domino cascade. Application of the process for the preparation of the stenoma alkaloid stenine was recently carried out in our laboratory.

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“…As an outgrowth of the above approach toward the erythrinane family, we undertook a subsequent study directed toward the synthesis of the lycorine type of alkaloids by utilizing the [4+2]-cycloaddition chemistry of furanyl carbamates [59]. Our synthetic strategy was to take advantage of an intramolecular Diels-Alder of an alkenyl-substituted furanyl carbamate derivative (IMDAF) [60,61]. In our approach to the core hexahydroindoline skeleton of this family of natural products, we examined the ringopening reaction of an aza-substituted oxabicyclo[2.2.1]heptene derivative.…”

Section: [4+2]-cycloaddition Chemistry Of Furanyl Carbamatesmentioning

confidence: 99%

Tandem methodology for heterocyclic synthesis

Padwa

2004

Pure and Applied Chemistry

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Tandem methodology for heterocyclic synthesis represents a powerful approach for the rapid buildup of molecular complexity from potentially simple starting materials. Work from our laboratory has shown that the rhodium(II)-catalyzed cyclization cascade of alpha-diazo imides represents an effective method for the synthesis of a variety of heterocyclic systems. As an extension of these studies, we became interested in using a linked Pummerer/N-acyliminium ion cyclization sequence since we felt that this combination offers unique opportunities for the assemblage of complex target molecules. A synthetic method that combines transformations of different reaction types significantly broadens the scope of such procedures in synthetic chemistry. Alpha-thiocarbocations generated from the Pummerer reaction of beta-phenylsulfinylmethyl-alpha, beta-unsaturated amides can be intercepted by the adjacent amido group to produce transient amino-substituted furans which undergo subsequent Diels–Alder cycloadditions. Using this domino amido Pummerer/Diels–Alder cascade, we were able to assemble novel polycyclic systems in a single operation. The key step in the process involves the generation of a reactive N-acyliminium ion by fragmentation of an amino-substituted [4+2]-cycloadduct. The successful synthesis of a number of alkaloids by this sequence of reactions reveals the usefulness and importance of this unique domino cascade. Application of the process for the preparation of the stenoma alkaloid stenine was recently carried out in our laboratory.

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Cycloaddition−Rearrangement Sequence of 2-Amido Substituted Furans as a Method of Synthesizing Hexahydroindolinones

Cited by 56 publications

References 40 publications

Aluminum‐Based Catalysts for Cycloaddition Reactions: Moving One Step Ahead in Sustainability

Aluminum‐Based Catalysts for Cycloaddition Reactions: Moving One Step Ahead in Sustainability

Tandem Methodology for Heterocyclic Synthesis

Tandem methodology for heterocyclic synthesis

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