160695-09-0Relevant articles and documents
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.
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.
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.
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.