Total synthesis of tryprostatins A and B

Yamakawa, Takayuki; Ideue, Eiji; Iwaki, Yuzo; Sato, Ayumu; Tokuyama, Hidetoshi; Shimokawa, Jun; Fukuyama, Tohru

doi:10.1016/j.tet.2011.05.112

Cited by 24 publications

(12 citation statements)

References 60 publications

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“…1 H NMR spectra were recorded with a Bruker Avance DPX 300 spectrometer at 29 °C and 300 MHz using Me 4 Si as an internal standard. IR spectra were obtained with a Bio-Rad FTS 3000MX as KBr pellets.…”

Section: Materials and Measurementsmentioning

confidence: 99%

“…1,2 Furthermore, gramine represents a valuable precursor for further derivatizations towards other targets, for example for the preparation of 1,3-disubstituted β-carbolines by the reaction of gramines with α-(alkylidenamino)nitriles in the presence of tributylphosphine 3 and for the synthesis of the 2-prenyl tryptophan core of the tryprostatins A and B. 4 For the quaternary gramine derivatives it was shown that they can be used as suitable sources of the 3-methylindole fragment in various diastereoselective alkylations, as recently described by Reinfelds et al 5 Gramine has also found utility as a part of N-substituted phosphines that were used as ligands in Suzuki-Miyaura coupling reactions of aryl halogenides, conducted at room temperature in a suitable ionic liquid, thus achieving increased yields in comparison with standard ligands containg amine groups. 6 Gramine derivatives also possess various biological activites; recently it was found that a gramine derivative (i.e…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Structural Evaluation of 5-Methyl-6-acetyl Substituted Indole and Gramine

Kukuljan

Kranjc

Perdih

2016

ACSi

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The synthesis and crystal structures of 1-(5-methyl-1H-indol-6-yl)ethan-1-one (7), C 11 H 11 NO, and 1-{3-[(dimethylamino)methyl]-5-methyl-1H-indol-6-yl}ethan-1-one (8), C 14 H 18 N 2 O, are reported. The synthesis is based on the Diels-Alder cycloaddition of a substituted 2H-pyran-2-one derivative, followed by an acid-catalyzed cyclization and concomitant deprotection (the last two steps were carried out as a one-pot domino process) yielding substituted indole 7, which was further derivatized via Mannich reaction to the gramine derivative 8. Both structures 7 and 8 were determined on the basis of IR, 1 H NMR and mass spectroscopy, as well as by the elemental analysis and melting point determination. According to the single-crystal X-Ray diffraction analysis, the structure 7 has a single unique molecule in the asymmetric unit whereas the structure 8 contains four unique molecules in the asymmetric unit. Molecules 7 are linked via N-H···O hydrogen bonds between the secondary amine group and carbonyl moiety of the acetyl group of adjacent molecules, whereas molecules 8 are linked via N-H···N hydrogen bonds between the secondary and tertiary amine groups of adjacent molecules. Both structures are further stabilized by weak C-H···O, C-H···π and π···π interactions.

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Section: Materials and Measurementsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and Structural Evaluation of 5-Methyl-6-acetyl Substituted Indole and Gramine

Kukuljan

Kranjc

Perdih

2016

ACSi

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“…The most commonly used synthetic strategies are either by addition of a prenyl moiety from prenyl bromide to a substrate, which was activated by strong base before, or by coupling reactions catalyzed by metal salts (Schkeryantz et al 1999;Yamakawa et al 2010;Zhao et al 2002). Both types of reactions are usually carried out under extreme conditions, e.g., anhydrous or anaerobic condition with special temperature control (Schkeryantz et al 1999;Yamakawa et al 2010;Zhao et al 2002). Even so, only some positions, e.g., N-1, C-2, and C-3 of the indole ring, are preferred by chemical prenylations.…”

Section: Introductionmentioning

confidence: 99%

“…C4-and C7-prenylated indole derivatives can be then obtained by rearrangements of C3-and N1-prenylated derivatives, respectively, under mild conditions (Schwarzer et al 2012(Schwarzer et al , 2013Thandavamurthy et al 2014). Meanwhile, additional steps are usually needed for protection and deprotection of the functional group in the reactants (Yamakawa et al 2010;Zhao et al 2012).…”

Section: Introductionmentioning

confidence: 99%

Impacts and perspectives of prenyltransferases of the DMATS superfamily for use in biotechnology

Fan

Winkelblech

2015

Appl Microbiol Biotechnol

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Prenylated compounds are ubiquitously found in nature and demonstrate interesting biological and pharmacological activities. Prenyltransferases catalyze the attachment of prenyl moieties from different prenyl donors to various acceptors and contribute significantly to the structural and biological diversity of natural products. In the last decade, significant progress has been achieved for the prenyltransferases of the dimethylallyltryptophan synthase (DMATS) superfamily. More than 40 members of these soluble enzymes are identified in microorganisms and characterized biochemically. These enzymes were also successfully used for production of a large number of prenylated derivatives. N1-, C4-, C5-, C6-, and C7-prenylated tryptophan and N1-, C2-, C3-, C4-, and C7-prenylated tryptophan-containing peptides were obtained by using DMATS enzymes as biocatalysts. Tyrosine and xanthone prenyltransferases were used for production of prenylated derivatives of their analogs. More interestingly, the members of the DMATS superfamily demonstrated intriguing substrate and catalytic promiscuity and also used structurally quite different compounds as prenyl acceptors. Prenylated hydroxynaphthalenes, flavonoids, indolocarbazoles, and acylphloroglucinols, which are typical bacterial or plant metabolites, were produced by using several fungal DMATS enzymes. Furthermore, the potential usage of these enzymes was further expanded by using natural or unnatural DMAPP analogs as well as by coexpression with other genes like NRPS and by development of whole cell biocatalyst.

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“…[24] Fukuyama's group has developed three 18 different syntheses for the 2-prenyl tryptophan core of tryprostatins along with their total syntheses, [25] but only the 19 one we report in Scheme 2 is worthy of attention. [25][26] The key step in this strategy is the selective radical-mediated 20 cyclization of isocyanide 24 that, along with a palladium-mediated coupling with a prenyl-group donor, lead to the …”

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confidence: 99%

Fungal Anticancer Metabolites: Synthesis Towards Drug Discovery

Barbero

Artuso

Prandi

2018

CMC

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This review summarizes the anticancer potential of fungal metabolites, highlighting the role of total 6 synthesis in sustaining their pharmacological development as an alternative to isolation. This paper also outlines the 7 feasibility of innovative synthetic procedures that facilitate the development of fungal metabolites into drugs that may 8 become a real future perspective. This review demonstrates that total chemical synthesis is a fruitful means of yielding 9 fungal derivatives as aided by recent technological and innovative advancements.

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Total synthesis of tryprostatins A and B

Cited by 24 publications

References 60 publications

Synthesis and Structural Evaluation of 5-Methyl-6-acetyl Substituted Indole and Gramine

Synthesis and Structural Evaluation of 5-Methyl-6-acetyl Substituted Indole and Gramine

Impacts and perspectives of prenyltransferases of the DMATS superfamily for use in biotechnology

Fungal Anticancer Metabolites: Synthesis Towards Drug Discovery

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