64584-92-5Relevant articles and documents
Asymmetric synthesis of (+)-stagonolide C and (-)-aspinolide A via organocatalysis
Shelke, Anil M.,Rawat, Varun,Suryavanshi, Gurunath,Sudalai, Arumugam
, p. 1534 - 1541 (2012)
A new enantioselective synthesis of two important fungal metabolites, (+)-stagonolide C and (-)-aspinolide A, has been described from readily available raw materials. Proline catalyzed asymmetric α-aminooxylation and Jorgensen's epoxidation of aldehydes a
Concise and protecting group-free synthesis of botryolide-E
Chandra Rao,Kumar Reddy,Shekhar,Venkateswarlu
, p. 828 - 829 (2013)
A simple highly concise protective group-free synthesis of botryolide-E from (R)-propylene oxide was developed using Hoveyda Grubbs cross metathesis, Still's modified Horner-Wadsworth-Emmons reaction, and Sharpless asymmetric dihydroxylation, as key steps.
Total synthesis of (–)-cephalosporolide D
Kalavakuntla, Chiranjeevi,Kummari, Vijaya Babu,Yadav, Jhillu Singh
, (2021/03/22)
In this communication, a concise and efficient synthetic route for the synthesis of (–)-Cephalosporolide D in enantioselective way has been described. In this synthesis, Mitsunobu esterification and Ring Closing Metathesis (RCM) for macrocyclic ring formation have been applied as key steps.
Copper-Catalyzed Enantiotopic-Group-Selective Allylation of gem-Diborylalkanes
Kim, Minjae,Park, Bohyun,Shin, Minkyeong,Kim, Suyeon,Kim, Junghoon,Baik, Mu-Hyun,Cho, Seung Hwan
supporting information, p. 1069 - 1077 (2021/01/25)
We report a copper-catalyzed enatiotopic-group-selective allylation of gem-diborylalkanes with allyl bromides. The combination of copper(I) bromide and H8-BINOL derived phosphoramidite ligand proved to be the most effective catalytic system to provide various enantioenriched homoallylic boronate esters, containing a boron-substituted stereogenic center that is solely derived from gem-diborylalkanes, in good yields with high enantiomeric ratios under mild conditions. Experimental and theoretical studies have been conducted to elucidate the reaction mechanism, revealing how the enatiotopic-group-selective transmetalation of gem-diborylalkanes with chiral copper complex occurs to generate chiral α-borylalkyl-copper species for the first time. Additional synthetic applications to the synthesis of various chiral building blocks are also included.
A Unified Synthetic Approach to Optically Pure Curvularin-Type Metabolites
Allu, Srinivasa Rao,Banne, Sreenivas,Jiang, Jia,Qi, Na,Guo, Jian,He, Yun
, p. 7227 - 7237 (2019/06/07)
A unified and concise approach to the synthesis of nine curvularin-type metabolites and two analogues has been developed with few steps and high yields. Among them, sumalactones A-D were synthesized for the first time. The key steps in this approach inclu
A Short Synthesis of (+)-Brefeldin C through Enantioselective Radical Hydroalkynylation
Gn?gi, Lars,Martz, Severin Vital,Meyer, Daniel,Sch?rer, Robin Marc,Renaud, Philippe
supporting information, p. 11646 - 11649 (2019/08/30)
A very concise total synthesis of (+)-brefeldin C starting from 2-furanylcyclopentene is described. This approach is based on an unprecedented enantioselective radical hydroalkynylation process to introduce the two cyclopentane stereocenters in a single step. The use of a furan substituent allows a high trans diastereoselectivity to be achieved during the radical process and it contains the four carbon atoms C1–C4 of the natural product in an oxidation state closely related to the one of the target molecule. The eight-step synthesis requires six product purifications and it provides (+)-brefeldin C in 18 % overall yield.
A facile, efficient and selective deprotection of p-methoxy benzyl ethers using zinc (Ii) trifluoromethanesulfonate
Chandrasekhar, Choragudi,Rao, Mannam Subba,Sireesha, Reddymasu,Sreenivasulu, Reddymasu
, p. 955 - 958 (2019/11/22)
Deprotection is significant and conducted over mild reaction conditions, in order to restrict any more side reactions with sensitive functional groups as well as racemization or epimerization of stereo center because the protective groups are often cleaved at last stage in the synthesis. P-Methoxy benzyl (PMB) ether appears unique due to its easy introduction and removal than the other benzyl ether protecting groups. A facile, efficient and highly selective cleavage of P-methoxy benzyl ethers was reported by using 20 mole% Zinc (II) Trifluoromethanesulfonate at room temperature in acetonitrile solvent over 15-120 min. time period. To study the generality of this methodology, several PMB ethers were prepared from a variety of substrates having different protecting groups and subjected to deprotection of PMB ethers using Zn(OTf)2 in acetonitrile. In this methodology, zinc triflate cleaves only PMB ethers without affecting acid sensitivity, base sensitivity and also chiral epoxide groups.
Carbohydrate/DBU Cocatalyzed Alkene Diboration: Mechanistic Insight Provides Enhanced Catalytic Efficiency and Substrate Scope
Yan, Lu,Meng, Yan,Haeffner, Fredrik,Leon, Robert M.,Crockett, Michael P.,Morken, James P.
supporting information, p. 3663 - 3673 (2018/03/21)
A mechanistic investigation of the carbohydrate/DBU cocatalyzed enantioselective diboration of alkenes is presented. These studies provide an understanding of the origin of stereoselectivity and also reveal a strategy for enhancing reactivity and broadening the substrate scope.
Synthesis and Stereochemical Assignment of Arenolide
Liu, Xun,Sun, Chunrui,Mlynarski, Scott,Morken, James P.
supporting information, p. 1898 - 1901 (2018/04/16)
The convergent synthesis of candidate stereoisomers of the natural product arenolide was accomplished using recently developed catalytic boron-based reactions. Comparison of the spectral data for candidate structures with that reported for the authentic natural product revealed the likely stereostructure of the natural compound.
[1,3]thiazin-2-amine compounds as well as applications and pharmaceutical compositions thereof
-
Paragraph 0136-0138; 0140; 0142, (2018/04/21)
The invention relates to [1,3]thiazin-2-amine compounds as well as applications and pharmaceutical compositions thereof, and belongs to the field of BACE (beta-site amyloid precursor protein cleavingenzyme) inhibitors. The [1,3]thiazid-2-amine compounds are compounds, pharmaceutically acceptable salts, stereoisomers, solvates, or prodrugs represented by a formula (I), and the formula (I) is shownin the description. The [1,3]thiazin-2-amine compounds provided by the invention have good inhibiting effects on BACE, and can be used for the preparation of medicines for treating neurodegenerativediseases such as alzheimer diseases.