3‐Alkenyl‐oxindoles: Natural Products, Pharmaceuticals, and Recent Synthetic Advances in Tandem/Telescoped Approaches

Millemaggi, Alessia; Taylor, Richard J.K.

doi:10.1002/ejoc.201000643

Cited by 316 publications

(102 citation statements)

References 105 publications

(110 reference statements)

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“…[19] We therefore decided to investigate the preparation of heterocyclic CA4 analogues containing a stereochemically defined substituted exocyclic alkene, by using these palladium-catalyzed domino processes. [20] We first planned to synthesize CA4 analogues with a heterocycle fused to the B-ring by using the tandem Heck carbocyclization/Suzuki cross-coupling process (Scheme 1). As we previously reported, under the optimized reaction conditions [Pd(OAc) 2 , PPh 3 , CsF] this tandem reaction occurred with the N-protected propynamide 6 c and the N-free butynamides 6 a and 6 b as starting materials.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and Structure–Activity Relationships of Constrained Heterocyclic Analogues of Combretastatin A4

et al. 2011

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A series of combretastatin A4 (CA4) analogues with a lactam or lactone ring fused to the trimethoxyphenyl or the B-phenyl moiety were synthesized in an efficient and stereoselective manner by using a domino Heck-Suzuki-Miyaura coupling reaction. The vascular-disrupting potential of these conformationally restricted CA4 analogues was assessed by various in vitro assays: inhibition of tubulin polymerization, modification of endothelial cell morphology, and disruption of endothelial cell cords. Compounds were also evaluated for their growth inhibitory effects against murine and human tumor cells. B-ring-constrained derivatives that contain an oxindole ring (in contrast to compounds with a benzofuranone ring) as well as analogues bearing a six-membered lactone core fused to the trimethoxyphenyl ring are endowed with significant biological activity. The most potent compound of this series (oxindole 9 b) is of particular interest, as it combines chemical stability and a biological activity profile characteristic of a vascular-disrupting agent.

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Section: Chemistrymentioning

confidence: 99%

Synthesis and Structure–Activity Relationships of Constrained Heterocyclic Analogues of Combretastatin A4

et al. 2011

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“…3b). For example, a novel class of receptor tyrosine kinase inhibitors synthesized from 3-alkenyl oxindole and has been used as anticancer and arthritis drugs 43 . Our laboratories are interested in plant viruses that cause detrimental effects on agriculture and horticulture 44 .…”

Section: Resultsmentioning

confidence: 99%

Metal and carbene organocatalytic relay activation of alkynes for stereoselective reactions

et al. 2014

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Transition metal and organic catalysts have established their own domains of excellence. It has been expected that merging the two unique domains should provide complimentary or unprecedented opportunities in converting simple raw materials to functional products. N-heterocyclic carbenes alone are excellent organocatalysts. When used with transition metals such as copper, N-heterocyclic carbenes are routinely practiced as strong-coordinating ligands. Combination of an N-heterocyclic carbene and copper therefore typically leads to deactivation of either or both of the two catalysts. Here we disclose the direct merge of copper as a metal catalyst and N-heterocyclic carbenes as an organocatalyst for relay activation of alkynes. The reaction involves copper-catalysed activation of alkynes to generate ketenimine intermediates that are subsequently activated by an N-heterocyclic carbene organocatalyst for stereoselective reactions. Each of the two catalysts (copper metal catalyst and N-heterocyclic carbene organocatalyst) accomplishes its own missions in the activation steps without quenching each other.

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“…A similar methodology was applied by the same research group for the synthesis of antiprotealide (22, Scheme 2), an omuralide-salinosporamide-type proteasome inhibitor: [19b] the same type of transformation was accomplished by treatment of the acrylamide 20 with the Kulinkovich reagent, generated in situ from Ti(OiPr) 4 and cyclopentylmagnesium bromide, followed by iodinolysis. The obtained α-iodomethyl γ-lactam could easily be converted into the desired α-methylene γ-lactam 21 under basic conditions, and the product 21, formed as single diastereoisomer, was further transformed into antiprotealide (22) in eight steps.…”

Section: Intramolecular Baylis-hillman Reactions In Syntheses Of α-Almentioning

confidence: 99%

“…Recent reviews by Janecki [3a] and by Feray and Bertrand [3b] briefly summarize synthetic methods leading to α-alkylidene γ-lactams through Wittig or Horner-Wadsworth-Emmons olefination reactions and radical-and transition-metal-mediated cyclizations, respectively. In turn, Millemaggi and Taylor devoted their 2010 review [4] to the biological activities and syntheses of natural and synthetic 3-alkenyloxindoles, which are a specific group of α-alkylidene γ-lactams.…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in the Synthesis of α‐Alkylidene‐Substituted δ‐Lactones, γ‐Lactams and δ‐Lactams

2011

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α-Alkylidene-substituted δ-lactones and corresponding γ-and δ-lactams constitute important classes of natural compounds that display diverse biological activities. This review gives a brief description of the occurrence and biological activities of the title compounds and then summarizes the methods available for their preparation. Attention is given mainly to the synthetic approaches developed during the last decade, including those from our own research group. The latest developments in the synthesis of nonracemic α-alkylidene-substituted δ-lactones, γ-lactams and δ-lactams are also discussed.

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3‐Alkenyl‐oxindoles: Natural Products, Pharmaceuticals, and Recent Synthetic Advances in Tandem/Telescoped Approaches

Cited by 316 publications

References 105 publications

Synthesis and Structure–Activity Relationships of Constrained Heterocyclic Analogues of Combretastatin A4

Synthesis and Structure–Activity Relationships of Constrained Heterocyclic Analogues of Combretastatin A4

Metal and carbene organocatalytic relay activation of alkynes for stereoselective reactions

Recent Advances in the Synthesis of α‐Alkylidene‐Substituted δ‐Lactones, γ‐Lactams and δ‐Lactams

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