Total synthesis of the Cephalotaxus alkaloids. Problem in nucleophilic aromatic substitution

Semmelhack, M. F.; Chong, B. P.; Stauffer, Richard D.; Rogerson, T.D.; CHONG, A. O.; Jones, L.

doi:10.1021/ja00842a031

Cited by 170 publications

(62 citation statements)

References 12 publications

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“…Several elegant syntheses of 1 have been reported over the past three decades. The racemic approaches have embodied several key transformations, including Nazarov cyclization, [19] photo-stimulated S RN 1 cyclization, [20] Claisen rearrangement, [21,22] oxidative ring contraction, [23] acylnitroso Diels-Alder cycloaddition, [24,25] transannular N-conjugate addition, [26,27] intramolecular alkyne hydroamination, [28] and reductive ring expansion of tetrahydrosioquinoline intermediates. [29,30] Non-racemic routes have featured electrophilic aromatic substitution, [31] Heck arylation, [32,33] Pummerer-electrophilic aromatic substitution cascade, [34][35][36] and acid catalyzed ring expansion of cyclobutanol derivatives.…”

mentioning

confidence: 99%

Synthesis of Antiproliferative Cephalotaxus Esters and Their Evaluation against Several Human Hematopoietic and Solid Tumor Cell Lines: Uncovering Differential Susceptibilities to Multidrug Resistance

Eckelbarger

Wilmot

Epperson

et al. 2008

Chemistry A European J

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Deoxyharringtonine (2), homoharringtonine (3), homodeoxyharringtonine (4), and anhydroharringtonine (5) are reported to be among the most potent members of the antileukemia alkaloids isolated from the Cephalotaxus genus. Convergent syntheses of these four natural products are described, each involving novel synthetic methods and strategies. These syntheses enabled evaluation of several advanced natural and non-natural compounds against an array of human hematopoietic and solid tumor cells. Potent cytotoxicity was observed in several cell lines previously not challenged with these alkaloids. Variations in the structure of the ester chain within this family of alkaloids confer differing activity profiles against vincristine-resistant HL-60/RV+, signalling new avenues for molecular design of these natural products to combat multi-drug resistance.

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mentioning

confidence: 99%

Synthesis of Antiproliferative Cephalotaxus Esters and Their Evaluation against Several Human Hematopoietic and Solid Tumor Cell Lines: Uncovering Differential Susceptibilities to Multidrug Resistance

Eckelbarger

Wilmot

Epperson

et al. 2008

Chemistry A European J

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“…On the basis of biogenetically patterned sequences [224] racemic dihydroerysodine (226) and erythratidine (227) …”

Section: Erythrina Alkaloidsmentioning

confidence: 99%

Alkaloids

Hoshino¹,

Murakata²,

Ishizaki³

et al. 2000

Ullmann's Encyclopedia of Industrial Chemistry

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“…Intramolecular enolate anion photoarylations, probed by Semmelhack,<250,251,) have found important application as a synthetically useful cyclization methodology. synthetic studies where cyclization of the iodoaryl-enolate 344 produced cephalotaxinone (250). Additional reactions illustrating the versatility and limitations of the methodology are outlined in equations (43) …”

Section: -mentioning

confidence: 99%