127758-25-2Relevant articles and documents
Highly active chiral ruthenium catalysts for asymmetric cross- and ring-opening cross-metathesis
Berlin, Jacob M.,Goldberg, Steven D.,Grubbs, Robert H.
, p. 7591 - 7595 (2006)
Metathesis takes sides: The scope of asymmetric metathesis has been expanded with the use of chiral ruthenium catalysts for asymmetric ring-opening cross-metathesis and for the first example of an asymmetric cross-metathesis (see scheme, TIPS = triisoprop
Asymmetric total syntheses of naturally occurring α,β-enone-containing RALs, L-783290 and L-783277 through intramolecular base-mediated macrolactonization reaction
Chakraborty, Joy,Ghosh, Ankan,Nanda, Samik
, p. 2331 - 2345 (2020/04/07)
Asymmetric total synthesis of two naturally occurring α,β-enone containing RALs, L-783290 and L-783277 is described in this article. An E-selective Horner-Wadsworth-Emmons (HWE) olefination was used as a key reaction to construct the C7′-C8′ olefinic unsaturation in L-783290. An enantiopure alkyne addition to the aldehyde followed by Z-selective partial reduction was employed to construct the C7′-C8′ olefinic unsaturation in L-783277. Biomimetic lactonization reaction was used to construct the macrolactone core in both the target molecules.
A natural ɑ - glucosidase inhibitor Penasulfate A synthetic method (by machine translation)
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Paragraph 0029; 0038; 0039, (2019/02/04)
The invention provides a natural ɑ - glucosidase inhibitor Penasulfate A synthetic method, including by the 1, 12 - dodecanediol via 5 step synthesis 12 - thirteen carbon olefine acid, L - arabinose via the 3 step synthesis (2 S, 3 R) - 2, 3 - oxygen - isopropyl - 4 - pentene - 1, 2, 3 - triol, (S)- Roche ester via the 8 step synthesis of chiral methyl undecenyl fundamental frequency that mellow boron ester, 12 - thirteen alkenylene acid and (2 S, 3 R) - 2, 3 - oxygen - isopropyl - 4 - pentene - 1, 2, 3 - triol in GrubbsII catalyst under the action of the olefin metathesis reaction, and then with the (R)- piperidine - 2 - carboxylic acid methyl ester reaction to prepare amide, re-oxidation results in the aldehyde, Takai alkene alkylation by thirteen alkenylene iodide, with the insecticidal compositions of the fundamental frequency that chiral methyl mellow boron ester in Pd (PPh3 )4 Catalytic, ethyl alcohol thallium as alkali under the condition of the key Suzuki coupling, hydrogenation reduction, [...], sulfuric acid ester, shall Penasulfate A. The present invention provides natural product Penasulfate A throughout the synthetic route for the first time, the olefin metathesis reactions and Suzuki coupling as a key reaction, the line is comparatively simple high efficiency, a high degree of convergence, the operation is easy to grasp. (by machine translation)
First asymmetric total synthesis of aspergillide D
Jena, Bighnanshu K.,Reddy, G. Sudhakar,Mohapatra, Debendra K.
supporting information, p. 1863 - 1871 (2017/03/09)
The first asymmetric total synthesis of a 16-membered macrolide, aspergillide D, is described. The chiral centers of the acid are derived from d-ribose and the alcohol subunit from 1,8-octane diol through Sharpless kinetic resolution, respectively. The other key reactions include Yamaguchi esterification, ring-closing metathesis reaction, and Shiina macrolactonization to construct the fully functionalized macrocycle.
D-erythro-sphingosine synthesis method
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, (2017/08/31)
The invention relates to a D-erythro-sphingosine synthesis method, comprising the steps of dissolving a compound 6 into dry tetrahydrofuran, adding lithium aluminum hydride under protection of nitrogen, after complete reaction of a raw material, adding a potassium sodium tartrate solution and finishing; extracting through ethyl acetate, concentrating and performing column chromatography; separating to obtain D-erythro-sphingosine. Compared with a traditional method, the synthesis method provided by the invention has the advantages that the use of a large amount of strong base phenyl lithium in a Wittig reaction process is avoided, meanwhile, the yield is increased; an azidation reaction adopts a two-step method of iodination and then azidation, and low temperature reaction in the existing technical scheme is not needed, so that the operation is more convenient and simple.
Diversity-Oriented Synthesis of cis -3,4-Dihydroxylated Piperidine and Its Higher Saturated and Unsaturated Homologues from d -Ribose and Their Glycosidase-Inhibition Study 1
Ajay, Sama,Arora, Inderpreet,Saidhareddy, Puli,Shaw, Arun K.
, p. 2721 - 2725 (2016/11/30)
The synthesis of six-, seven-, and eight-membered cis-dihydroxy azacycles has been accomplished from d-ribose using Vasella reductive amination as a key step and utilization of hydroboration-oxidation, Mitsunobu reaction, and ring-closing metathesis (RCM) reactions in a facile manner. These homologous dihydroxylated heterocyclic scaffolds were subjected to the glycosidase inhibition assays. However, only a moderate inhibitory activity for three out of five compounds was observed against α-glucosidases with a high degree of selectivity.
Chiron Approaches to the Antitumor Natural Product Fuzanin D
Gao, Yangguang,Cao, Zhou,Su, Chengzhong,Chen, Zefeng,He, Xianran,Ding, Fei,Li, Hang,Zhang, Yongmin
, p. 4471 - 4476 (2016/12/14)
Fuzanin D, a pyridine-containing natural product, which exhibits cytotoxic activity against DLD-1 cells, is synthesized in a concise manner using l-arabinose or ethyl l-lactate as chiral pool substrates in nine steps (14.4% overall yield) and six steps (30.8% overall yield), respectively. The key steps involve Wittig olefination and olefin cross--metathesis.
Chiral approach to total synthesis of phytotoxic and related nonenolides: (Z)-isomer of (6S,7R,9R)-6,7-dihydroxy-9-propylnon-4-eno-9-lactone, herbarumin-III and their C-9 epimers
Maram, Lingaiah,Parigi, Raghavendar Reddy,Das, Biswanath
, p. 7135 - 7142 (2016/10/22)
A new and efficient strategy has been developed for the stereoselective total synthesis of nonenolides: (Z)-isomer of (6S,7R,9R)-6,7-dihydroxy-9-propylnon-4-eno-9-lactone, herbarumin-III and their C-9 epimers starting from D (?) ribose. The synthesis includes the coupling of the alcohol and acid fragments of the molecules, employing Yamaguchi esterification protocol followed by intramolecular ring closure metathesis. The method has efficiently constructed the 10-membered lactone skeleton of the compounds with proper stereogenic centers containing appropriate functionalities.
A concise synthesis of the dihydroxy styryllactone, 7-epi-goniodiol
Zeng, PingLi,Wang, Dong,Zhou, Junhui,Dong, Zhibing
, p. 331 - 334 (2016/07/06)
A short and efficient stereoselective synthesis of dihydroxy styryllactone 7-epi-goniodiol has been achieved in nine steps and 20% overall yield, starting from readily available L-erythrose monoacetonide. The key steps of the synthesis involved a stereoco
A stereoselective total synthesis of xyolide, a natural bioactive nonenolide
Maram, Lingaiah,Das, Biswanath
, p. 674 - 682 (2015/06/02)
A stereoselective total synthesis of xyolide, a naturally occurring bioactive nonenolide, has been accomplished. The acid fragment of the molecule has been prepared from D-mannitol and the alcohol fragment from (2Z)-but-2-ene-1,4-diol. The synthesis invol