1200-93-7Relevant articles and documents
Ruthenium-NHC-Diamine Catalyzed Enantioselective Hydrogenation of Isocoumarins
Li, Wei,Wiesenfeldt, Mario P.,Glorius, Frank
, p. 2585 - 2588 (2017)
A novel and practical chiral ruthenium-NHC-diamine system is disclosed for the enantioselective hydrogenation of isocoumarins, which provides a new concept to apply (chiral) NHC ligands in asymmetric catalysis. A variety of optically active 3-substituted 3,4-dihydroisocoumarins were obtained in excellent enantioselectivities (up to 99% ee). Moreover, this methodology was utilized in the synthesis of O-methylmellein, mellein, and ochratoxin A.
Organocatalytic Aerobic Oxidation of Benzylic sp3 C-H Bonds of Ethers and Alkylarenes Promoted by a Recyclable TEMPO Catalyst
Zhang, Zhiguang,Gao, Yuan,Liu, Yuan,Li, Jianjun,Xie, Hexin,Li, Hao,Wang, Wei
, p. 5492 - 5495 (2015)
An entirely metal-free catalyst system consisting of an easily prepared recyclable new TEMPO derived sulfonic salt catalyst, and mineral acids (NaNO2 and HCl) has been developed for selective aerobic oxidation of structurally diverse benzylic sp3 C-H bonds of ethers and alkylarenes. The mild reaction conditions allow for the generation of synthetically and biologically valued isochromanones and xanthones from readily accessible alkyl aromatic precursors in good yields.
Synthesis of pseudodeflectusin and ustusorane C: Structural revision of aspergione A and B
Kuramochi, Kouji,Saito, Fumiyo,Nakazaki, Atsuo,Takeuchi, Toshifumi,Tsubaki, Kazunori,Sugawara, Fumio,Kobayashi, Susumu
, p. 1635 - 1640 (2010)
The syntheses of racemic and optically active pseudodeflectusin and ustusorane C are described. The 1H-and 13C-NMR data for our synthetic pseudodeflectusin and ustusorane C were identical to those of the corresponding natural product
Synthesis of (R)-mellein by a partially reducing iterative polyketide synthase
Sun, Huihua,Ho, Chun Loong,Ding, Feiqing,Soehano, Ishin,Liu, Xue-Wei,Liang, Zhao-Xun
, p. 11924 - 11927 (2012)
Mellein and the related 3,4-dihydroisocoumarins are a family of natural products with interesting biological properties. The mechanisms of dihydroisocoumarin biosynthesis remain largely speculative today. Here we report the synthesis of mellein by a partially reducing iterative polyketide synthase (PR-PKS) as a pentaketide product. Remarkably, despite the head-to-tail homology shared with several fungal and bacterial PR-PKSs, the mellein synthase exhibits a distinct keto reduction pattern in the synthesis of the pentaketide. We present evidence to show that the ketoreductase (KR) domain alone is able to recognize and differentiate the polyketide intermediates, which provides a mechanistic explanation for the programmed keto reduction in these PR-PKSs.
Isocoumarin derivative as well as preparation method and medical application thereof
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Paragraph 0249-0253; 0262-0265, (2020/03/17)
The invention belongs to the technical field of chemical medicines, and relates to an isocoumarin compound of general formula (I) and a preparation method and medical application, of the isocoumarin compound in preparation of medicines for treating and mo
The scent of bacteria: Headspace analysis for the discovery of natural products
Citron, Christian A.,Rabe, Patrick,Dickschat, Jeroen S.
, p. 1765 - 1776 (2013/01/15)
Volatile compounds released by 50 bacterial strains, 45 of them actinobacteria in addition to three chloroflexi and two myxobacteria, have been collected by use of a closed-loop stripping apparatus, and the obtained headspace extracts have been analyzed by GC-MS. Excluding terpenes that have recently been published elsewhere, 254 compounds from all kinds of compound classes have been identified. For unambiguous compound identification several reference compounds have been synthesized. Among the detected volatiles 12 new natural products have been found, in addition to mellein, which was released by Saccharopolyspora erythraea. The iterative PKS for this compound has recently been identified by in vitro experiments, but mellein production in S. erythraea has never been reported before. These examples demonstrate that headspace analysis is an important tool for the discovery of natural products that may be overlooked using conventional techniques. The method is also useful for feeding experiments with isotopically labeled precursors and was applied to investigate the biosynthesis of the unusual nitrogen compound 1-nitro-2-methylpropane, which arises from valine. Furthermore, several streptomycetes emitted compounds that were previously recognized as insect pheromones, thus questioning if bacterial symbionts are involved in insect communication.