Total Synthesis of Aqabamycin G, a Nitrophenyl Indolylmaleimide Marine Alkaloid from Vibrio sp. WMBA

Abstract

The first total synthesis of the marine alkaloid aqabamycin G is disclosed. The synthetic sequence involved the stepwise addition to maleimide of an indole motif and a substituted diazo-benzenoid unit derived from acetaminophen. An alternative strategy using a protected phenol is also reported.

Marine natural products

“…[68][69][70][71] Two structural revisions of bacterial MNPs were reported in 2022; the absolute congurations of the cyclic peptides ogipeptin A 237 and tumescenamide A 238 were corrected via total synthesis. 72,73 Other total syntheses of bacterial NPs included cyanogramides A and C, 74 (±)-nesteretal A, 75 lucentamycin A together with barmumycin, oxotomaymycin and oxoprothracarcin, 76 rakicidin F, 77,78 anthracimycin and anthracimycin B, 79 xiamycins C-F, 80 seongsanamide E, 81 salimabromide, 82 (+)-nocardioazine B, 83 the indolocarbazole alkaloid ZHD-0501, 84 (±)-spiroindimicins A, D, G and H, 85 bahamaolide A, 86 aqabamycin G, 87 and elmonin and pratenone A. 88 Reviews focused on marine bacterial NPs published during 2022 included publications on the biosynthesis of microbial terpenoids, 89 polyketides and non-ribosomal peptides, 90 ribosomal peptides, 91 and the anthracyclines.…”

Electrochemically promoted thio-Michael addition of N-substituted maleimides to thiols in an aqueous medium

“…Maleimides and succinimides are versatile construction motifs in numerous natural products, and play important roles in the development of pharmaceuticals and pesticides. [1][2][3][4][5] For instance, compounds with a maleimide-like core serve as potential neuroprotective agents, 6 anticancer drugs, 7 and antiinflammatory agents. 8 In addition, they are also valuable pharmaceutical and chemical intermediates, and can be converted into pyrrolidine, pyrrolidone, lactam, and other related compounds.…”