194610-24-7Relevant articles and documents
Convergent approach to (E)-alkene and cyclopropane peptide isosteres
Wipf, Peter,Xiao, Jingbo
, p. 103 - 106 (2007/10/03)
(Chemical Equation Presented) Trisubstituted (E)-alkene isosteres (TEADIs) and novel cyclopropane amide bond isosteres (CPDIs) were synthesized by aldimine addition and three-component aldimine addition-cyclopropanation methodologies, respectively. These
Imine additions of internal alkynes for the synthesis of trisubstituted (E)-alkene and cyclopropane peptide isosteres
Wipf, Peter,Xiao, Jingbo,Geib, Steven J.
, p. 1605 - 1613 (2007/10/03)
Divergent multi-component reactions (DMCR) involving C-C bond formations can provide large increases in structural diversity and allow the rapid assembly of complex products from readily available starting materials. Cascade hydrozirconation-Zr/Zn transmetalation-imine addition of alkynes represents a versatile methodology for the synthesis of (E)-alkene and cyclopropane dipeptide isosteres. Appropriate substitutions at the sp2-carbon of (E)-alkene peptide isosteres allow a range of Pd-catalyzed cross-coupling reactions, which can be used for the fine-tuning of the conformational and electronic properties of the parent peptide bond mimic. C-C bond formation by microwave-accelerated Stille coupling of stannylalkenes represents a fast, convergent synthetic approach toward trisubstituted (E)-alkene dipeptide isosteres.
Synthesis of the J ring segment of gambieric acid
Kadota, Isao,Takamura, Hiroyoshi,Yamamoto, Yoshinori
, p. 3649 - 3651 (2007/10/03)
The J ring segment 2 of gambieric acid was synthesized stereoselectively by the coupling between the cyclic ether component 3 and the alkenyl iodide 4. The tetrahydropyran 3 was stereoselectively synthesized by the 6-endo-cyclization of a hydroxyepoxide prepared from deoxy-D-ribose. The side chain moiety 4 was prepared by the stereoselective hydrostannation of an internal alkyne.
Synthetic studies of an 18-membered antitumor macrolide, tedanolide. 5. Stereoselective synthesis of the C13 - C23 part via condensation of two fragments, C13 - C17 and C18 - C21, by taking advantage of the 3,4- dimethoxybenzyl protecting group
Zheng, Bao-Zhong,Maeda, Hiroshi,Mori, Michiko,Kusaka, Shin-Ichi,Yonemitsu, Osamu,Matsushima, Tomohiro,Nakajima, Noriyuki,Uenishi, Jun-Ichi
, p. 1288 - 1296 (2007/10/03)
An efficient and stereoselective synthesis of the C13 - C23 part (8) was achieved starting from methyl (R) - and (S)-3-hydroxy-2-methylpropionates (9) via coupling of the C13 - C17 aldehyde (6), prepared by Evans asymmetric aldol reaction, with the C18 - C21 iodoalkene (5b) by taking advantage of the 3,4-dimethoxybenzyl protecting group.