Liposidomycins − Synthetic Studies Towards the Ribosyldiazepanone Moiety

Abstract

A synthesis of the enantiopure 2-ribosyl-1,4-diazepan-3-one core of liposidomycins, a class of complex lipid nucleoside antibiotics, according to a flexible asymmetric synthesis strategy is described. It involves two building blocks, an enantiopure α-azido-β,γ-epoxybutanol readily available from L-

Synthesis of New Trifluoromethylated Hydroxyethylamine‐Based Scaffolds

“…In most of these cases, yields and the diversity of amino acids used were poor. [32][33][34][35][36][37][38][39][40][41][42][43][44][45] Currently, there are only two efficient methods for this reaction. The first one involves the use of Ca(OTf) 2 as a promoter of the reaction.…”

Total Synthesis of (−)‐Caprazamycin A

“…Construction of the syn ‐β‐hydroxy amino acid moiety with an S configuration at C5′ was then investigated. Several strategies have been employed for this in the past,5d,e, 6g,i–k, 7a, 8a two of which were used for the total synthesis of caprazol. One is a Sharpless asymmetric aminohydroxylation of the α,β‐unsaturated ester7a and the other is the diastereoselective isocyanoacetate aldol reaction 8a.…”

Caprazamycins: Promising lead structures acting on a novel antibacterial target MraY

“…The central diazepanone ring in caprazamycin (14, Figure 4) plays a critical anchoring role, orienting the other subunits and facilitating their highly specific interactions within MraY's active site [47]. As the diazepanone ring adds further complexity to synthesis however [48][49][50][51][52][53][54][55], its isosteric substitution with both cyclic and acyclic, or complete removal, are being investigated for use as diazepanone substitutes. 3) [56].…”