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Stereocontrolled Synthesis of Arylomycin-Based Gram-Negative Antibiotic GDC-5338
We report herein
an efficient, stereocontrolled, and chromatography-free
synthesis of the novel broad spectrum antibiotic GDC-5338. The route features the construction of a functionalized tripeptide
backbone, a high-yielding macrocyclization via a Pd-catalyzed Suzuki–Miyaura
reaction, and the late-stage elaboration of key amide bonds with minimal
stereochemical erosion. Through extensive reaction development and
analytical understanding, these key advancements allowed the preparation
of GDC-5338 in 17 steps, 15% overall yield, >99 A
% HPLC,
and >99:1 dr
FIGURE 42 in 5338
FIGURE 42. Copulatory organs of Otacilia striata sp. nov.: A. Male left palp, ventral view; B. Same, retrolateral view; C. Same, dorsal view; D. Epigyne, ventral view; E. Same, dorsal view. Scale bars: 0.2 mm.Published as part of Mu, Yannan & Zhang, Feng, 2023, 5338, pp. 1-104 in Zootaxa 5338 (1) on page 55, DOI: 10.11646/zootaxa.5338.1.1, http://zenodo.org/record/828373
FIGURE 36 in 5338
FIGURE 36. Copulatory organs of Otacilia spina sp. nov.: A. Male left palp, ventral view; B. Same, retrolateral view; C. Same, dorsal view; D. Epigyne, ventral view; E. Same, dorsal view. Scale bars: 0.2 mm.Published as part of Mu, Yannan & Zhang, Feng, 2023, 5338, pp. 1-104 in Zootaxa 5338 (1) on page 47, DOI: 10.11646/zootaxa.5338.1.1, http://zenodo.org/record/828373
FIGURE 81 in 5338
FIGURE 81. Male left palp of Xilithus pugious sp. nov.: A. Ventral view; B. Retrolateral view; C. Dorsal view; D. Retro-dorsal view. Scale bars: 0.2 mm.Published as part of Mu, Yannan & Zhang, Feng, 2023, 5338, pp. 1-104 in Zootaxa 5338 (1) on page 95, DOI: 10.11646/zootaxa.5338.1.1, http://zenodo.org/record/828373
FIGURE 21 in 5338
FIGURE 21. Copulatory organs of Otacilia allomanubrium sp. nov.: A. Male left palp, ventral view; B. Same, retrolateral view; C. Same, dorsal view; D. Epigyne, ventral view; E. Same, dorsal view. Scale bars: 0.2 mm.Published as part of Mu, Yannan & Zhang, Feng, 2023, 5338, pp. 1-104 in Zootaxa 5338 (1) on page 30, DOI: 10.11646/zootaxa.5338.1.1, http://zenodo.org/record/828373
FIGURE 67 in 5338
FIGURE 67. Habitus of Punctus taibai sp. nov.: A. Male holotype, dorsal view; B. Same, ventral view; C. Female paratype, dorsal view; D. Same, ventral view.Published as part of Mu, Yannan & Zhang, Feng, 2023, 5338, pp. 1-104 in Zootaxa 5338 (1) on page 81, DOI: 10.11646/zootaxa.5338.1.1, http://zenodo.org/record/828373
FIGURE 40 in 5338
FIGURE 40. Habitus of Otacilia striata sp. nov.: A. Male holotype, dorsal view; B. Same, ventral view; C. Female paratype, dorsal view; D. Same, ventral view.Published as part of Mu, Yannan & Zhang, Feng, 2023, 5338, pp. 1-104 in Zootaxa 5338 (1) on page 53, DOI: 10.11646/zootaxa.5338.1.1, http://zenodo.org/record/828373
FIGURE 22 in 5338
FIGURE 22. Habitus of Otacilia guposhan sp. nov.: A. Male holotype, dorsal view; B. Same, ventral view; C. Female paratype, dorsal view; D. Same, ventral view.Published as part of Mu, Yannan & Zhang, Feng, 2023, 5338, pp. 1-104 in Zootaxa 5338 (1) on page 31, DOI: 10.11646/zootaxa.5338.1.1, http://zenodo.org/record/828373
FIGURE 66 in 5338
FIGURE 66. Epigyne of Pennalithus palgongensis (Seo, 1988): A. Dorsal view; B. Ventral view.Published as part of Mu, Yannan & Zhang, Feng, 2023, 5338, pp. 1-104 in Zootaxa 5338 (1) on page 80, DOI: 10.11646/zootaxa.5338.1.1, http://zenodo.org/record/828373
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