40914-18-9Relevant academic research and scientific papers
Revision of the structure and total synthesis of altenuisol
Nemecek, Gregor,Cudaj, Judith,Podlech, Joachim
, p. 3863 - 3870 (2012/09/25)
A total synthesis of the reported structure of altenuisol is described. Comparison of the 1H NMR spectra of the synthesized compound and of the natural product revealed that the originally proposed structure was not correct. Consequently, two constitutional isomers were synthesized. The spectra of one of these compounds - a structure originally proposed as the structure of altertenuol - matched perfectly with the spectra of the natural product. The total synthesis of altenuisol was thus achieved starting with phloroglucinic acid and protocatechuic aldehyde in 10 steps and in 23% yield, where the longest linear sequence consisted of 6 steps. The key step was a Suzuki coupling with concomitant formation of the lactone ring. Whether altertenuol is identical with altenuisol could not be decided. Total synthesis of altenuisol, a minor toxin in ubiquitous Alternaria spp. revealed that the originally proposed structure was not correct. Altenuisol was proved to have an isomeric structure by total synthesis. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
New approach for the construction of the coumarin frame and application in the total synthesis of natural products
Jerezano, Alberto,Jimenez, Fabiola,Del Carmen Cruz, Maria,Montiel, Luisa E.,Delgado, Francisco,Tamariz, Joaquin
, p. 185 - 198 (2011/04/17)
A new synthetic approach is described for building the coumarin scaffold through the Lewis acid-promoted cyclization of novel aryl 3-(dimethylamino)prop- 2-enoates 2a - 2f. The latter precursors were prepared via aminomethylenation of the corresponding aryl acetates 4a - 4f with the Bredereck reagent. This approach was used for the synthesis of biologically active natural compounds 1a - 1f, through a three-step procedure starting from the corresponding phenols.
Synthesis of lamellarin U and lamellarin G trimethyl ether by alkylation of a deprotonated α-aminonitrile
Liermann, Johannes C.,Opatz, Till
, p. 4526 - 4531 (2008/09/21)
(Chemical Equation Presented) 1,2,3,4-Tetrahydroisoquinoline-1- carbonitriles can serve as starting materials for the one-pot synthesis of 5,6-dihydropyrrolo[2,1a]isoquinolines and 1-benzyl-3,4-dihydroisoquinolines. The latter compounds were transformed to lamellarin G trimethyl ether and lamellarin U in short reaction sequences. This method allows the introduction of acid-sensitive protecting groups for the phenolic hydroxy functions which would be cleaved under the harsh conditions of the classical Bischler-Napieralski reaction.
Synthesis of dictyomedins using phosphazene base catalyzed diaryl ether formation
Ebisawa, Masaru,Ueno, Masahiro,Oshima, Yoshiteru,Kondo, Yoshinori
, p. 8918 - 8921 (2008/03/14)
Dictyomedins isolated from dictyostelium cellular slime molds were synthesized by using diaryl ether derivatives as key intermediates for the cyclization to dibenzofuran followed by palladium catalyzed intramolecular biaryl formation.
Antimitotic and cell growth inhibitory properties of combretastatin A-4-like ethers
Lawrence, Nicholas J.,Rennison, David,Woo, Meiki,McGown, Alan T.,Hadfield, John A.
, p. 51 - 54 (2007/10/03)
A series of diarylamines, diaryl and arylbenzyl ethers based on combretastatin A-4 was prepared and evaluated for anticancer activity. 2-Methoxy-5-(3',4',5'-trimethoxyphenoxymethyl)phenol was the most active (IC50, K562 20 nM) and caused significant G2/M cell cycle arrest. (C) 2000 Elsevier Science Ltd.
