Enantio and diastereoselective total synthesis of all four stereoisomers of germicidin N

Marine natural products

“…87 The rst synthesis of germicidin N, along with three other stereoisomers, followed by detailed NMR data matching, enabled the structure of the MNP to be conrmed, although specic rotation comparison showed a large discrepancy between synthetic and natural material and this observation is now under further investigation. 91 Over 35 reviews featuring some aspect of marine bacteria chemistry or biology were published during 2020. Some review highlights included those describing the role of class I adenylate-forming enzymes in biosynthesis, 93 the discovery and importance of glycosylated NPs from marine microbes, 94 the potential of MNPs as monoamine oxidase inhibitors (including their activities and selectivity) and implications for neurodegenerative disease research, 95 the evolution of chemoenzymatic syntheses with a focus on meroterpenoids from Streptomyces species, 96 the importance of terpene synthases to the structural diversity of terpenoid NPs, 97 combating nematode infections using MNPs from epiphytic bacteria, 98 the biology and chemical diversity of tetramic acid derivatives from marine microbes, 99 an overview of bacterial tropone-derived NPs, 100 bacteria sourced NP contributions in the ght against mosquitotransmitted tropical diseases, 101 and an outline of the challenges and opportunities associated with the application of symbiotic microbes to the discovery of novel antibiotics.…”

“…The first total syntheses of six bacterial compounds were reported in the literature during 2020, included sunshinamide 261 , 87 jomthonic acid A, 88 tumescenamide C, 89 (−)-anthracimycin, 90 germicidin N, 91 and seongsanamide B. 92 The total synthesis of sunshinamide 261 enabled the configuration of the previously unassigned stereogenic centre to be determined, although large differences in the specific rotations at the same concentrations and solvent (−1.5 (MNP) vs. −37.1 (synthetic)) for the isolated and synthesised compounds could not be reconciled.…”

“…87 The first synthesis of germicidin N, along with three other stereoisomers, followed by detailed NMR data matching, enabled the structure of the MNP to be confirmed, although specific rotation comparison showed a large discrepancy between synthetic and natural material and this observation is now under further investigation. 91…”