Fulicineroside, an Unusual Glycosidic Dibenzofuran Metabolite from the Slime Mold <i>Fuligo cinerea </i>(Schwein.) Morgan

Řezanka, Tomáš; Hanŭs, L; Kujan, Petr; Dembitsky, Valery M.

doi:10.1002/ejoc.200400870

Cited by 23 publications

(12 citation statements)

References 27 publications

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“…297 The total synthesis of (+)-fulicineroside 315 was accomplished and reported in 2013. The total synthesis was started with the Ullman-type coupling 298 commercially available resorcin 312 with readily accessible 1-bromo-3,5-dimethoxybenzene 311 to obtain the corresponding biarylether phenol as an intermediate which without isolation is transformed into the dimethyl carbamate 313 via a one-pot fashion.…”

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confidence: 99%

Total synthesis of natural products containing benzofuran rings

et al. 2017

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Research on natural products containing benzofuran has remarkably increased during the past few decades.Newly isolated natural products with complex structures are being studied, characterized and screened for possible biological activities. Several of such compounds have exhibited various biological activities, thus their total syntheses have attracted much attention from synthetic organic chemists. In this review, we aim to highlight the origins, structures, biological potencies, and synthetic approaches of those natural products bearing at least one benzofuran in their complex structures. Furthermore, we especially focus on the step in which this key heterocycle is installed during the total synthesis of a natural product as the desired target.

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confidence: 99%

Total synthesis of natural products containing benzofuran rings

et al. 2017

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“…2-Methylbutyric acid was determined on a capillary column with a stationary chiral phase, this time by gas chromatography as described previously. [32] These results suggest the structure of 1, which was partially determined, and show that the absolute configuration of two out of the three chiral centers is (5R,1ЈЈS). (Figure 3).…”

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confidence: 92%

Identification of the Eight‐Membered Heterocycles Hicksoanes A–C from the Gorgonian Subergorgia hicksoni

et al. 2008

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Novel eight‐membered heterocycles, named hicksoanes A–C, were isolated from the gorgonian Subergorgia hicksoni. Their structures, including the absolute configuration of all three stereocenters, were determined by means of extensive spectroscopic data. Hicksoanes have a unique structure containing a triazocane cycle, which is substituted by isoleucine and tryptophan moieties. Hicksoanes A–C showed antifeeding activity against goldfish at natural concentration (≈10 μg mL–1).(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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“…Synthesis of the trisaccharide : Structure 50 was proposed for the trisaccharide part of fulicineroside (Figure 3). 1 The β‐glycosidic linkage between L ‐rhodinose and L ‐rhamnose is unprecedented in natural products. For comparison reasons the corresponding trisaccharide 51 with the α‐glycosidic linkage was also chosen as a synthetic target.…”

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confidence: 99%

“…Discussion of NMR spectroscopic data for the aglycone fulicinerine (2) and the natural product fulicineroside (1) : With the completed structures of fulicinerine ( 2 ) and its epoxy diastereomer 49 in hand, a detailed comparison of our NMR spectroscopic data with those published by Řezanka1 was accomplished.…”

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confidence: 99%

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Total Synthesis of the Postulated Structure of Fulicineroside

Bartholomäus

Dommershausen

Thiele

et al. 2013

Chemistry A European J

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A total synthesis of the proposed structures of fulicineroside and its aglycone fulicinerine is reported. The tetrasubstituted dibenzofuran substructure was accessible either through a Pd-mediated ortho-metalation or by an Ir-catalyzed meta-borylation. The synthesis of the β,β,α-linked trisaccharide consisting of D-olivose, L-rhodinose, and L-rhamnose was challenged by the unprecedented β-linked rhodinose. A Pd-catalyzed β-selective glycosylation of a 4-epi-rhodinose and a subsequent Mitsunobu inversion provided selectively the β-linked L-rhodinose-L-rhamnose disaccharide. Comparison with the reported data for the natural product and the aglycone suggests a misassignment of the structure of the natural product.

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Fulicineroside, an Unusual Glycosidic Dibenzofuran Metabolite from the Slime Mold Fuligo cinerea (Schwein.) Morgan

Cited by 23 publications

References 27 publications

Total synthesis of natural products containing benzofuran rings

Total synthesis of natural products containing benzofuran rings

Identification of the Eight‐Membered Heterocycles Hicksoanes A–C from the Gorgonian Subergorgia hicksoni

Total Synthesis of the Postulated Structure of Fulicineroside

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