3521-91-3Relevant articles and documents
A fortuitously straightforward synthesis of 4-acetoxy-2-propyltetrahydrothiophene
Ma, Bianbian,Yang, Shaoxiang,Tao, Feiyan,Sun, Baoguo,Liu, Yongguo,Tian, Hongyu
, p. 724 - 726 (2015)
4-Acetoxy-2-propyltetrahydrothiophene was synthesised from 1-hepten-4-ol by a three-step route involving epoxidation and mesylation to 1,2-epoxy-4-heptyl mesylate and then reaction with thioacetate. An acetoxylated cyclic product was formed instead of the expected thioacetate, and a mechanism for its formation using an intramolecular transesterification is proposed.
Toward creation of a universal NMR database for stereochemical assignment: The case of 1,3,5-trisubstituted acyclic systems
Kobayashi, Yoshihisa,Tan, Choon-Hong,Kishi, Yoshito
, p. 2562 - 2571 (2000)
Using the diastereoisomeric triols 1a-d (Fig. 1) and examples summarized in Fig. 2, the central C-atom of acyclic 1,3,5-triols is demonstrated to exhibit a distinctive chemical shift that is dependent on the 1,3- and 3,5-relative configuration, but is independent of the functionalities present outside of this structural motif. These NMR characteristics are then used to predict the relative configuration of several natural products (Fig, 7). In addition, an example is given to show the possibility of assembling an NMR database for a larger array of functional groups from NMR databases of smaller arrays of functional groups.
Oxa/thiazole-tetrahydropyran triazole-linked hybrids with selective antiproliferative activity against human tumour cells
Valdomir, Guillermo,Fernández,Lagunes, Irene,Padrón, Juan I.,Martín, Víctor S.,Padrón, José M.,Davyt, Danilo
supporting information, p. 13784 - 13789 (2018/08/21)
Inspired by diverse marine bioactive compounds, the principle of molecular hybridization was applied to produce a series of new compounds combining diverse heterocyclic systems (oxa/thiazoles and tetrahydropyrans) via a triazole ring, attempting to increase the activity of individual building blocks. These new compounds exhibit a highly interesting antiproliferative activity against different human tumour cells and good selectivity when compared to normal cells. The formation of reactive oxygen species and the interaction with P-gp were also evaluated for the lead compounds.
Short stereoselective synthesis of (+)-monocerin via a palladium-catalysed intramolecular alkoxycarbonylation
Punganuru, Surendra R.,Aviraboina, Sivaprasad,Srivenugopal, Kalkunte S.
, p. 375 - 378 (2016/07/06)
A concise stereoselective total synthesis of (+)-monocerin has been accomplished using cross metathesis, tandem dihydroxylation-SN2 cyclisation and intramolecular alkoxycarbonylation as key steps. Cross-metathesis of 2-iodo-3,4,5-trimethoxyvinylbenzene and (R)-hepten-4-ol, followed by tandem dihydroxylation-SN2 cyclisation generated a tri-substituted tetrahydrofuran ring. Finally, the dihydroisocoumarin was obtained by an intramolecular alkoxycarbonylation. In this paper, we have developed an expedient operationally simple Pd(OAc)2/bathocuproine catalysed alkoxycarbonylation under atmospheric pressure of carbon monoxide. The catalytic system developed here can be useful for the synthesis of various dihydroisocoumarins and phthalides.
