18498-59-4Relevant academic research and scientific papers
An efficient synthesis of fluorocyclopentenes using fluoroalkylidenecarbenes
Guan, Tong,Takemura, Kohei,Senboku, Hisanori,Yoshida, Masanori,Hara, Shoji
, p. 76 - 79 (2008)
An efficient synthesis of fluorocyclopentenes is described. By treatment of (2-fluoroalkenyl)iodonium salts with potassium tert-butoxide, (α-fluoroalkylidene)carbenes were generated efficiently to give fluorocyclopentenes via 1,5-C-H insertion. Fluorocyclopentenes having a functionality, such as chlorine, acetoxy, or ketone, and a spiro fluorocyclopentene were synthesized in good yields.
A highly convergent cascade cyclization to cis-hydrindanes with all-carbon quaternary centers and its application in the synthesis of the aglycon of dendronobiloside A
Han, Yejian,Zhu, Lizhi,Gao, Yuan,Lee, Chi-Sing
, p. 588 - 591 (2011)
An efficient and versatile ZnBr2-catalyzed Diels-Alder/ carbocyclization cascade reaction has been developed for construction of highly functionalized cis-hydrindanes (70-96% yields with high diastereoselectivity), and it has been successfully utilized in the synthesis of the aglycon of dendronobiloside A.
Allenes as dipolarophiles in the intramolecular carbene cyclization-cycloaddition cascade reaction
Zhang, Xingxian,Ko, Rebecca Y. Y.,Li, Shuoliang,Miao, Ru,Chiu, Pauline
, p. 1197 - 1200 (2006)
Intramolecular carbene cyclization-cycloaddition cascade reactions with allenes occur efficiently in the presence of dirhodium catalysts to afford oxatricyclic products as single diastereomers. Georg Thieme Verlag Stuttgart.
In(OTf)3-Catalyzed Cascade Cyclization for Construction of Oxatricyclic Compounds
Bao, Wenli,Tao, Yezi,Cheng, Jiangqun,Huang, Junrong,Cao, Jingming,Zhang, Mengxun,Ye, Weijian,Wang, Bo,Li, Yang,Zhu, Lizhi,Lee, Chi-Sing
, p. 7912 - 7915 (2018)
A highly diastereoselective cascade cyclization reaction has been developed for establishing a series of oxatricyclic compounds using Chan's diene and simple keto alkynal substrates with only 1 mol % of In(OTf)3 as the catalyst in 82-92% yields. The potential utility of this synthetic strategy has been demonstrated in model studies for the construction the core structures of 1α,8α:4α,5α-diepoxy-4,5-dihydroosmitopsin and cortistatin A.
Biosynthesis of (R)-2-Hydroxybut-3-enylglucosinolate (Progoitrin) from 3H>But-3-enylglucosinolate in Brassica napus
Rossiter, John T.,James, David C.
, p. 1909 - 1913 (1990)
The synthesis of 3H>but-3-enylglucosinolate is described and its role in (R)-2-hydroxybut-3-enyl-glucosinolate biosynthesis is discussed.This is the first time radio labelled but-3-enylglucosinolate has been synthesized and its incorporation into (R)-2-hydroxybut-3-enylglucosinolate demonstrated.
Absolute Configuration of Curacin A, a Novel Antimitotic Agent from the Tropical Marine Cyanobacterium Lyngbya majuscula
Nagle, Dale G.,Geralds, Robin S.,Yoo, Hye-Dong,Gerwick, William H.,Kim, Tae-Seong,et al.
, p. 1189 - 1192 (1995)
Curacin A is a structurally novel antimitotic agent isolated from the Caribbean cyanobacterium Lyngbya majuscula.Its planar structure has been previously determined from a spectroscopic investigation, Here, we define the complete relative and absolute configuration of curacin A by comparison of products obtained from chemical degradation of the natural product with the same substances prepared by synthesis.Curacin A is shown to have 2R, 13R, 19R, 21S absolute configuration.
Total synthesis of ceratopicanol through tandem cycloaddition reaction of a linear substrate
Lee, Sang-Shin,Kim, Won-Yeob,Lee, Hee-Yoon
, p. 2450 - 2456,7 (2012)
Total synthesis of ceratopicanol (1) was achieved with a tandem cycloaddition reaction of allenyl diazo compound 6 via a trimethylenemethane (TMM) diyl intermediate. The TMM diyl mediated [2+3] cycloaddition reaction furnished the consecutive quaternary c
The Tandem Bergman-Radical Cyclization: A New Method For Ring Annulation
Grissom, Janet Wisniewski,Calkins, Trevor L.
, p. 2315 - 2318 (1992)
Heating of enediynes 1a, 1b and 2 at 210 deg C in a sealed tube in the presence of a hydrogen atom source yields naphthalene derivatives 3a, 3b and 4 in yields of 53-72 percent.
Synthesis of an Alkynyl Methylglyoxal Probe to Investigate Nonenzymatic Histone Glycation
David, Yael,Guber, David,Maksimovic, Igor,Upad, Akhil,Zheng, Qingfei
, (2020)
Methylglyoxal (MGO) is a reactive dicarbonyl metabolite that modifies histones in vivo and induces changes in chromatin structure and function. Here we report the synthesis and application of a chemical probe for investigating MGO-glycation. A two-step synthesis of a Cu-click compatible alkynyl oxoaldehyde probe (AlkMGO) via sequential Dess-Martin and Riley oxidations is presented. This synthesis elevates the accessibility and utility of an important tool for tracking, enriching, and studying MGO-glycation to aid in understanding its underlying biochemical functions.
A dramatic effect of the reaction conditions on the course of a palladium-catalyzed cyclization of an alkene bearing a vinyl bromide and a nucleophile: A new route to the trans-hydrindane system
Coudanne, Isabelle,Castro, Jaume,Balme, Geneviève
, p. 995 - 997 (1998)
Upon treatment with catalytic Pd(dppe) in the presence of KH, the malonate derivative 3 underwent a Wacker-type cyclization leading exclusively to compound 4 having the trans-hydrindane system. However, the course of the cyclization is dramatically dependent on the reaction conditions, mainly on the nature of the base. In the presence of a carbonate, a quaternary ammonium salt and the catalytic system (Pd(OAc)2 + PPh3) the cyclization of the same substrate 3 led only to compounds resulting from an initial Heck reaction of the vinyl bromide on the neighbouring olefin.
