160695-09-0Relevant academic research and scientific papers
Synthesis and antibacterial activity of a novel series of acylides: 3-O-(3-pyridyl)acetylerythromycin A derivatives
Tanikawa, Tetsuya,Asaka, Toshifumi,Kashimura, Masato,Suzuki, Keiko,Sugiyama, Hiroyuki,Sato, Masakazu,Kameo, Kazuya,Morimoto, Shigeo,Nishida, Atsushi
, p. 2706 - 2715 (2007/10/03)
A novel series of acylides, 3-O-(aryl)acetylerythromycin A derivatives, were synthesized and evaluated. These compounds have significant potent antibacterial activity against not only Gram-positive pathogens, including inducibly macrolide-lincosamide-stre
Enantiopure polycycles by sequential cycloadditions
Wolter, Martina,Borm, Claudia,Merten, Erik,Wartchow, Rudolf,Winterfeldt, Ekkehard
, p. 4051 - 4060 (2007/10/03)
The enolsilyl ether 2, generated from butynone adduct 3, which is easily available from the enantiomerically pure cyclopentadiene 1, proved to be a general building block for polycyclic anellation products to cyclohexenone. After proper adjustment of functional groups in the cycloadducts by means of high pressure Diels-Alder cycloadditions, the thermal retro-process provided routes to various enantiopure alicyclic and heterocyclic target compounds in high yields.
Enantiopure building blocks for marine natural products via differentiation of enantiotopic groups
Beil, Winfried,Jones, Peter G.,Nerenz, Frank,Winterfeldt, Ekkehard
, p. 7273 - 7292 (2007/10/03)
The group and face-selective cycloaddition of the enantiopure cyclopentadiene 4 to the tyrosine-related spirocylohexadienone 10 provided a high yield of the enantiomencally pure cyclohexadienone 11. Stereoselective transformations at the remaining double bond followed by a thermal retro- process, finally giving rise to the chromophore of the marine agelorin antibiotics isolated from the sponge Agelas oroides Schmidt.
Use of Winterfeldt's template to control the C-2' configuration in the synthesis of strigol-type compounds
Roehrig, Susanne,Hennig, Lothar,Findeisen, Matthias,Welzel, Peter,Mueller, Dietrich
, p. 3439 - 3456 (2007/10/03)
A route comprising (i) a cycloaddition reaction of citraconic anhydride with the Winterfeldt auxiliary, (ii) hydride reduction of the cycloadduct, (iii) a (formal) ether formation, and (iv) a cycloreversion reaction allows efficient stereocontrol at C-2' in the synthesis of strigol and its structural analogues.
A predictable enantioselective total synthesis of (+)-clavularin A
Weinmann,Winterfeldt
, p. 1097 - 1101 (2007/10/02)
Cycloadduct 9 was transformed into vinylsilane 11d in a conjugate addition-alkylation sequence. Epoxidation and subsequent hydrolysis provided the clavularin adduct 14, which on flash vacuum pyrolysis (FVP) gave (+)-clavularin A (1) in 91% yield.
Face-Selective and endo-Selective Cycloadditions with Enantiomerically Pure Cyclopentadienes
Beckmann, Marion,Meyer, Thorsten,Schulz, Frauke,Winterfeldt, Ekkehard
, p. 2505 - 2510 (2007/10/02)
A general synthetic route to the enantiopure bicyclic cyclopentadienes (S)-3 and (R)-3 of the hydrindane series, starting from the Hajos-Wiechert ketone 4 or its enantiomer is described.Reasons for the excellent face and endo selectivity of cycloadditions
Enantiopure Didemnenones via Kinetic Resolution
Goeres, Markus,Winterfeldt, Ekkehard
, p. 3525 - 3532 (2007/10/02)
Kinetic resolution in an enantioselective Diels-Alder process provided the starting material for an imporved and simplified approach to all the didemnenones via the lactone 16.
