Two new tryptamine-derived alkaloids from Chimonanthus praecox f. concolor

Kitajima, Mariko; Mori, Ikue; Arai, Kazumichi; Kogure, Noriyuki; Takayama, Hiromitsu

doi:10.1016/j.tetlet.2006.03.047

Cited by 138 publications

(61 citation statements)

References 14 publications

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“…Short-step manipulation of 26 provided debromoflustraminol B 26 and CPC-1 (Scheme 9). 27 Thus, treatment of 26 with prenyl bromide followed by exhaustive deacylation afforded 28, which on reductive methylation yielded debromofrustraminol B, a marine alkaloid from Flustra foliacea (L.). In addition, methylation of 26 followed by removal of the acetyl group provided 29, which upon reductive methylation, formed CPC-1 isolated from Chimonanthus praecox f. 28 …”

Section: Synthesis Of Pyrroloindole Alkaloidsmentioning

confidence: 99%

Application of Electrochemically Generated Hypervalent Iodine Oxidant to Natural Products Synthesis

2013

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Hypervalent iodine oxidants have been widely applied in organic reactions due to their low toxicity, ready availability, and ease of handling. We produced an oxidant, [phenyliodine(III)bis(trifluoroethoxide)] (PIFE) by anodic oxidation of iodobenzene, which possesses comparable or superior properties to those of commercially available congeners, such as [phenyliodine(III)bis(trifluoroacetate)] (PIFA) and [phenyliodine(III)diacetate] (PIDA). The availability of PIFE was demonstrated by construction of several nitrogen-containing molecular skeletons; construction of quinolinone derivatives by PIFE occurred smoothly in moderate yield. In addition, the carbazole derivatives were synthesized in higher yields than with use of PIFA. Application of this methodology enabled synthesis of the bioactive tetrahydropyrroloiminoquinone-, carbazole-, and pyrroloindole-class natural products, including makaluvamines, damirones, glycozoline, debromofrustraminol B, and CPC-1.

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Section: Synthesis Of Pyrroloindole Alkaloidsmentioning

confidence: 99%

Application of Electrochemically Generated Hypervalent Iodine Oxidant to Natural Products Synthesis

2013

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“…Isopropanol-mediated transfer hydrogenation of allyl acetate, α-methyl allyl acetate or 1,1,-dimethylallene as allyl donors, in the presence of the substituted isatins delivered the anticipated products of allylation, crotylation, and tert -prenylation, respectively, in highly enantiomerically enriched form. Notably, highly enantioselective allylation, crotylation, and reverse prenylation of isatins employing conventional allylmetal reagents have not been reported (Scheme 27) (For enantioselective catalytic allylation of isatins, see: [310]).…”

Section: Iridium-catalyzed Transfer Hydrogenation For C–c Bond Formmentioning

confidence: 99%

Formation of C–C Bonds via Iridium-Catalyzed Hydrogenation and Transfer Hydrogenation

2010

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The formation of C-C bonds via catalytic hydrogenation and transfer hydrogenation enables carbonyl and imine addition in the absence of stoichiometric organometallic reagents. In this review, iridium-catalyzed C-C bond-forming hydrogenations and transfer hydrogenations are surveyed. These processes encompass selective, atom-economic methods for the vinylation and allylation of carbonyl compounds and imines. Notably, under transfer hydrogenation conditions, alcohol dehydrogenation drives reductive generation of organoiridium nucleophiles, enabling carbonyl addition from the aldehyde or alcohol oxidation level. In the latter case, hydrogen exchange between alcohols and π-unsaturated reactants generates electrophile-nucleophile pairs en route to products of hydro-hydroxyalkylation, representing a direct method for the functionalization of carbinol C-H bonds.

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“…15 In order to explore this chemistry a C3a-hydroxy pyrroloindoline was required. While a number of methods have been reported for the synthesis of C3a-hydroxy pyrroloindolines, 8e,8f,12a,16 the oxidation reported by Takayama and co-workers 17 which employs m -CPBA and TFA seemed to provide the most direct access. When protected tryptamine 6 was exposed to these conditions a 59% yield of pyrroloindoline 7 was obtained.…”

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confidence: 99%

Lewis Acid Catalyzed Displacement of Trichloroacetimidates in the Synthesis of Functionalized Pyrroloindolines

Adhikari

Chisholm

2016

Org. Lett.

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The pyrroloindoline core is found in many natural products. These structures often differ at the C3a position, which may be substituted with an oxygen, nitrogen, sp3 or sp2 hybridized carbon. Utilizing a trichloroacetimidate leaving group, a diversity-oriented approach to these structures has been developed. The trichloroacetimidate intermediate allows for the rapid incorporation of anilines, alcohols, thiols and carbon nucleophiles. This method was applied in the synthesis of arunidinine and a formal synthesis of psychotriasine.

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Two new tryptamine-derived alkaloids from Chimonanthus praecox f. concolor

Cited by 138 publications

References 14 publications

Application of Electrochemically Generated Hypervalent Iodine Oxidant to Natural Products Synthesis

Application of Electrochemically Generated Hypervalent Iodine Oxidant to Natural Products Synthesis

Formation of C–C Bonds via Iridium-Catalyzed Hydrogenation and Transfer Hydrogenation

Lewis Acid Catalyzed Displacement of Trichloroacetimidates in the Synthesis of Functionalized Pyrroloindolines

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