131675-63-3Relevant academic research and scientific papers
Alkylative aziridine ring-opening reactions
Choi, Jieun,Ha, Hyun-Joon,Yu, Taehwan
, (2021)
In this study, the highly strained three-membered aziridine ring was successfully activated as the aziridinium ion by alkylation of the ring nitrogen with a methyl, ethyl or allyl group, which was followed by ring opening with external nucleophiles such as acetate and azide. Such alkylative aziridine ring opening provides an easy route for the synthesis of various N-alkylated aminecontaining molecules with concomitant introduction of an external nucleophile at either its α- or β-position.
Total synthesis of calicheamicin γ1I. 1. Synthesis of the oligosaccharide fragment
Groneberg,Miyazaki,Stylianides,Schulze,Stahl,Schreiner,Suzuki,Iwabuchi,Smith,Nicolaou
, p. 7593 - 7611 (2007/10/02)
The first total synthesis of the calicheamicin γ1I oligosaccharide fragment in the form of its methyl glycoside (62) has been achieved. The synthetic challenge of the B-ring was recognized and studied initially, resulting in a novel and unique solution to the stereochemical problems posed involving a [3,3]-sigmatropic rearrangement of an allylic thionoimidazolide (111). This chemistry was initially worked out on a model for the ABC-ring system (47) and then successfully applied to the real system. The success of this synthesis has enabled the completion of the first synthesis of the natural product itself, calicheamicin γ1I (1), as will be described in the following papers in this issue.
