Enantioselective first total syntheses of the antiviral natural products xiamycins D and E

Abstract

The enantioselective first total synthesis of marine pentacyclic indolosesquiterpenoids xiamycins D (4) & E (5) has been described. The synthetic approach features functionalization of enantiopure Wieland-Miescher ketone, Michael addition followed...

Marine natural products

“…The first total syntheses of 22 marine bacterial compounds was reported in the literature during 2021, caprolactin C 6 , 5 akazaoxime 4 and A-76356 45 , 16 MA026 67 , 25 xiamycins D and E, 69 bacicyclin, 70 (+)-pseudonocardide A and (+)-pseudonocardide C, 71 nocardiotide A, 72 three 2-( p -hydroxybenzyl)-prodigiosin-based MNPs, along with isoheptylprodigiosin, and tambjamine MYP1, 73 (+)-spiroindimicin A, 74 nesteretal A, 75 (+)-03219A, 76 enterocin, 77 nahuoic acid A, 78 piscibactin, 79 and aldgamycin N. 80…”

Metal-Catalyzed C–H Bond Oxidation in the Total Synthesis of Natural and Unnatural Products

“…58 In 2021, Dethe and Shukla accomplished the first total synthesis of xiamycins D and E using Sanford's methodology through the reaction between compound 98, Pd(OAc) 2 , and PhI(OAc) 2 to deliver compound 99 in 64% yield (Scheme 27). 60 Scheme 27 C-H oxidation in the total synthesis of (+)-xiamycins D (101) and E (100)…”

Construction of an Angular Tricyclic Benzofuran Skeleton Using the C–H Activation Strategy

“…C–H activation − is a potent tool that is increasingly used in the total synthesis of natural products. − Recently, we redesigned a protocol for skeleton construction by employing a C–H bond activation strategy. Compared with previous protocols, the total syntheses of these natural products and various derivatives were more efficient and the total yields were remarkably higher.…”