- Natural product Pimprinine derivative as well as preparation method and application thereof
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The invention discloses a Pimprinine derivative as shown in a formula III in the description. The invention also discloses a preparation method of the Pimprinine derivative, and a series of Pimprinine derivatives are synthesized by taking Pimprinine as a lead, combining the structural characteristics of Pimprinine, taking cheap and easily available indole as a raw material, modifying and transforming different sites of a framework structure of the indole and introducing different substituent groups. The Pimprinine derivative disclosed by the invention has good bactericidal activity, shows efficient and/or broad-spectrum bactericidal activity, and can be applied to crop diseases caused by fungi, bacteria and viruses.
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Paragraph 0052-0055; 0062
(2021/07/31)
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- First reported propylphosphonic anhydride (T3P) mediated Robinson–Gabriel cyclization. Synthesis of natural and unnatural 5-(3-indolyl)oxazoles
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In the present work, a propylphosphonic anhydride (T3P) assisted Robinson–Gabriel cyclization of N-acyl-β-oxotryptamines for the synthesis of 2-substituted-5-(3-indolyl)oxazoles has been developed. The reactions proceeded smoothly in acetonitri
- Szabó, Tímea,Dancsó, András,ábrányi-Balogh, Péter,Volk, Balázs,Milen, Mátyás
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p. 1353 - 1356
(2019/04/27)
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- A 5 - (3 - indolyl) - oxazole compound of preparation method
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The invention discloses a preparation method of a 5-(3-indolyl)-oxazole compound with a structure as shown in the formula (I). The method comprises the following step: in the presence of iodine and dimethyl sulfoxide, a compound with a structure as shown in the formula (II) and a compound with a structure as shown in the formula (III) undergo a contact reaction. Raw materials used in the preparation method are cheap and easily available. The preparation method is simple and the preparation step is short. In addition, the contact reaction can be carried out by a one kettle way during synthetic operation. Yield is high and can reach 84%. The preparation method provided by the invention is especially suitable for industrial production.
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Paragraph 0060; 0061; 0062; 0063
(2017/09/12)
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- One-pot total synthesis: The first total synthesis of chiral alkaloid pimprinol A and the facile construction of its natural congeners from amino acids
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In this work, we accomplished the first total synthesis of chiral alkaloid pimprinol A and the facile construction of its natural congeners: pimprinine, pimprinethine, pimprinaphine, WS-30581A, WS-30581B, laboradorin 1, uguenenazole, balsoxine, texamine in one-pot from commercially available starting materials including amino acids. Further investigating into the mechanism revealed that this improved transformation was achieved by the integration of iodination, Kornblum oxidation, condensation, decarboxylation, annulation, and oxidation reaction sequence.
- Xiang, Jiachen,Wang, Jungang,Wang, Miao,Meng, Xianggao,Wu, Anxin
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p. 7470 - 7475
(2014/12/10)
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- Synthesis of 5-(3-indolyl)oxazole natural products. Structure revision of Almazole D
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The synthesis and utility of β-oxotryptamine and β-oxytryptophan ester synthons provide a convenient entry to 5-(3-indolyl)oxazole natural products leading to a structure revision of almazole D.
- Miyake, Fumiko,Hashimoto, Michinao,Tonsiengsom, Sorasaree,Yakushijin, Kenichi,Horne, David A.
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experimental part
p. 4888 - 4893
(2010/08/06)
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- A facile synthesis of naturally occurring 5-(3-indolyl)oxazoles
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A simple and efficient synthesis of naturally occurring 5-(3-indolyl)oxazoles is described. The key steps of this convergent approach are the formation of a 3-tosyloxyacetyl-1-benzenesulfonylindole, a 3-amino-acetyl-1-benzenesulfonylindole hydrochloride a
- Kumar, Dalip,Sundaree, Swapna,Patel, Gautam,Rao
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p. 867 - 869
(2008/04/13)
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- Synthesis of oxazolylindolyl alkaloids via rhodium carbenoids
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The oxazolylindole alkaloids pimprinine (1a), pimprinethine (1b) and WS-30581 A (1c) are readily obtained in two steps by rhodium(II) catalysed reaction of N-Boc-3-diazoacetylindole with the appropriate nitrile followed by removal of the Boc-group.
- Doyle,Moody
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p. 1021 - 1022
(2007/10/02)
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- Synthesis of Oxazolylindole Alkaloids from Tryptamine and Tryptophan by Oxidation with 2,3-Dichloro-5,6-dicyanobenzoquinone
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When N-acyl derivatives of tryptamine and L-tryptophan methyl ester were treated with DDQ (2 equiv) in tetrahydrofuran or other anhydrous solvents, four consecutive reactions, dehydrogenation, nucleophilic cyclization, another dehydrogenation, and isomeri
- Yoshioka, Tadao,Mohri, Kunihiko,Oikawa, Yuji,Yonemitsu, Osamu
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p. 2252 - 2281
(2007/10/02)
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