The Total Synthesis of (±)‐Fumimycin

Abstract

The antibiotic agent fumimycin has been synthesized for the first time. This natural product was found to inhibit the bacterial peptide deformylase and may represent a lead structure to a class of novel antibacterials. Our synthetic strategy towards fumimycin involved the following steps: Dakin oxidation of an aldehyde functionality, conversion of an oxime through radical fragmentation to form an N-diphenylphosphoryl group, construction of an α-trisubstituted amine by 1,2-addition to a ketimine, a Claisen rearrangement with subsequent transition-metal-catalyzed olefin isomerization to install a propenyl chain and final amidation.

Chromatography with silver nitrate: part 2

“…A potential invasive pest to North America is the pink gypsy moth Lymantria mathura, which produces as the major sex pheromone component, (-)-mathuralure (76). To support a population monitoring program of this moth, Britton 56 developed a gram-scale synthesis of this molecule starting from 1-dodecayne (77).…”

Synthesis of chiral N-phosphinyl α-imino esters and their application in asymmetric synthesis of α-amino esters by reduction

“…These resulted α-amino acid derivatives are useful building blocks in modern organic synthetic and medicinal chemistry [21–22]. For example, we can easily find the active participation of α-imino esters in the total synthesis of the bioactive molecule fumimycin [23]. Moreover, α-amino acids are the most general fragments constituting peptides and proteins, especially for human insulin [24–28].…”

Palladium‐Catalyzed Highly Chemoselective Cascade Coupling‐Cyclization of Allenol Derivatives and Aryl Halides for the Construction of Dihydrobenzofuranols or Chromanols and Indolinols

“…This reaction route was completely different from the one found by Alcaide et al. Moreover, the corresponding product dihydrobenzofuranol 3 is a fused‐aromatic heterocyclic compound, which has bactericidal,, antimicrobial, and pharmacological activity . Additionally, this compound also contains a functional group, such as an exocyclic double bond or a substituted styrene, which can be transformed for further diversification …”