444809-35-2Relevant articles and documents
Bioorthogonal Hydroamination of Push–Pull-Activated Linear Alkynes
Cheung, Sheldon T.,Kang, Dahye,Kim, Justin
, p. 16947 - 16952 (2021)
A bioorthogonal reaction between N,N-dialkylhydroxylamines and push–pull-activated halogenated alkynes is described. We explore the use of rehybridization effects in activating alkynes, and we show that electronic effects, when competing stereoelectronic and inductive factors are properly balanced, sufficiently activate a linear alkyne in the uncatalyzed conjugative retro-Cope elimination reaction while adequately protecting it against cellular nucleophiles. This design preserves the low steric profile of an alkyne and pairs it with a comparably unobtrusive hydroxylamine. The kinetics are on par with those of the fastest strain-promoted azide-alkyne cycloaddition reactions, the products regioselectively formed, the components sufficiently stable and easily installed, and the reaction suitable for cellular labeling.
A study toward a total synthesis of fostriecin
Kiyotsuka, Yohei,Igarashi, Junji,Kobayashi, Yuichi
, p. 2725 - 2729 (2007/10/03)
In order to synthesize the major C(3)-C(12) part of fostriecin, asymmetric dihydroxylation of several dienes 5a-f, prepared by cross-coupling reactions of several types, was studied, thus providing high dependency on the hydroxyl groups at C(5) and C(11). The best regioselectivity was obtained with 5d to produce diol 23, which was later transformed into the advanced intermediate 26.
