28120-76-5Relevant academic research and scientific papers
Total Synthesis of Isorosthin L and Isoadenolin I
Ao, Junli,Sun, Chao,Chen, Bolin,Yu, Na,Liang, Guangxin
, (2022/01/20)
Total syntheses of two Isodon diterpenes, isorosthin L and isoadenolin I, are reported. The synthetic strategy features a quick assembly of two simple building blocks through a diastereoselective intermolecular aldol reaction and a subsequent radical cyclization for efficient construction of a rather complex advanced intermediate bearing a quaternary stereocenter present in all Isodon diterpenes. Oxidative cleavage of the C?C bond in the cyclopentane enabled the conversion to a lactone moiety which is desired for the construction of the molecular skeleton through reductive coupling with an aldehyde carbonyl group.
Asymmetric Alkylation of Anthrones, Enantioselective Total Synthesis of (?)- and (+)-Viridicatumtoxins B and Analogues Thereof: Absolute Configuration and Potent Antibacterial Agents
Nicolaou,Liu, Guodu,Beabout, Kathryn,McCurry, Megan D.,Shamoo, Yousif
supporting information, p. 3736 - 3746 (2017/03/20)
A phase transfer catalyzed asymmetric alkylation of anthrones with cyclic allylic bromides using quinidine- or quinine-derived catalysts is described. Utilizing mild basic conditions and as low as 0.5 mol % catalyst loading, and achieving up to >99:1 dr selectivity, this asymmetric reaction was successfully applied to produce enantioselectively (?)- and (+)-viridicatumtoxins B, and thus allowed assignment of the absolute configuration of this naturally occurring antibiotic. While the developed asymmetric synthesis of C10 substituted anthrones is anticipated to find wider applications in organic synthesis, its immediate application to the construction of a variety of designed enantiopure analogues of viridicatumtoxin B led to the discovery of highly potent, yet simpler analogues of the molecule. These studies are expected to facilitate drug discovery and development efforts toward new antibacterial agents.
ENANTIOENRICHED VIRIDICATUMTOXIN B ANALOGS
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Page/Page column 84, (2017/11/10)
In one aspect, the present disclosure provides derivatives of viridicatumtoxin of the formula wherein the variables are as defined herein. Also provided herein are compositions and methods of treating a bacterial infection, a viral infection, or in the treatment of cancer. The present disclosure also provides methods of synthesizing enantiopure viridicatumtoxin and other anthrone compounds.
Improved synthesis of methyl 3-oxo-2,6,6-trimethylcyclohex-1-ene-1- carboxylate, an A-ring intermediate for (±)strigol
Qianchao,Shiqing, Pi,Xinzhi, Chen
, p. 494 - 496 (2008/09/21)
Methyl 3-oxo-2,6,6-trimethylcyclohex-1-ene-1-carboxylate was synthesised over eight steps from the starting material of citral instead of α-ionone. KMnO4, HC(OEt)3 and O2/TEMPO/CuCl were substituted for NaIO4, CH3I and pyridinium chlorochromate, respectively. Every step was simplified and gave a 48% overall yield. The procedure is suitable for large scale production.
γ-Pyronene, a synthon derived from saffron and intermediary precursor of synthesis of forskolin and strigol
Boulin,Arreguy-San Miguel,Delmond
, p. 2753 - 2762 (2007/10/03)
γ-Pyronene, a terpenic synthon available from myrcene, is an excellent raw material for the preparation of numerous intermediates used in the synthesis of perfumes, retinoids and biological derivatives such as forskolin or strigol.
Chemical studies on crude drug processing. IX. On the constituents of rehmanniae radix. (3). Absolute stereostructures of rehmaionosides A, B, and C, and rehmapicroside, biologically active ionone glucosides and a monoterpene glucoside isolated from Chine
Yoshikawa,Fukuda,Taniyama,Kitagawa
, p. 41 - 47 (2007/10/03)
Following the characterization of the iridoid and iridoid glycoside constituents in Chinese Rehmanniae Radix, the dried root of Rehmannia glutinosa LIBOSCH. [Kan-jio in Japanese], we investigated the structures of biologically active ionone glucosides, re
