Total Synthesis and Stereochemistry Assignment of Nucleoside Antibiotic A‐94964

Shao, Xuemei; Zheng, Ce; Xu, Peng; Shiraishi, Taro; Kuzuyama, Tomohisa; Molinaro, Antonio; Silipo, Alba; Yu, Biao

doi:10.1002/anie.202200818

Cited by 7 publications

(1 citation statement)

References 66 publications

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“…Au(I) catalyzed glycosylation with glycosyl ortho ‐alkynylbenzoates as donors is highly powerful and extremely mild, gaining widespread application in the synthesis of complex molecules. [ 23‐33 ] Thus, ortho ‐hexynylbenzoates 5 and 35 were synthesized by condensation of corresponding hemiacetals with ortho ‐ hexynylbenzoic acid in 92% and 98% yields, respectively (Scheme 5a, see Supporting Information for details). To our delight, coupling of disaccharide 33 with 5 under the action of Ph 3 PAuNTf 2 in toluene proceeded smoothly, resulting in trisaccharide 36 in an excellent 96% yield.…”

Section: Resultsmentioning

confidence: 99%

Total Synthesis of Starfish Cyclic Steroid Glycosides. Part 3, Formal Total Synthesis of Luzonicosides A and D

et al. 2023

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Luzonicosides A (1) and D (2) are the major saponins isolated from pacific starfish Echinaster Luzonicus, featuring a sterically congested 16-membered ring which is formed by bridging the C3 and C6 of a 3β,6β-dihydroxy-Δ 7 -ene steroid with a 1,2-trans-linked linear trisaccharide via glycosidic and ether bonds, respectively. Here, we describe a formal total synthesis of starfish cyclic steroid glycosides 1 and 2. The synthetic route is highly modular and versatile, involving construction of the 16-membered macrocycles via Au(I)-catalyzed intramolecular glycosylation, highly efficient installation of unsaturated sugar moieties with ortho-hexynylbenzoates, elaboration of glucuronic acid unit via post-oxidation, and a de novo synthesis of the ether-linked pyranose unit.

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Section: Resultsmentioning

confidence: 99%

Total Synthesis of Starfish Cyclic Steroid Glycosides. Part 3, Formal Total Synthesis of Luzonicosides A and D

et al. 2023

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Synthesis of the Reducing‐end Hexasaccharide Fragment of Marine Lipopolysaccharide Axinelloside A

Zhang,

Zeng,

Zhu

et al. 2024

Chemistry A European J

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Chemical synthesis of an orthogonally protected hexasaccharide relevant to the reducing‐end half of axinelloside A, a highly sulfated marine lipopolysaccharide, is disclosed. The synthesis features preparation of the scyllo‐inositol unit via a Ferrier‐type‐II rearrangement, construction of the 1,2‐cis‐glycosidic bonds via remote participation, and concise [2+2+2] assembly via Au(I)‐catalyzed glycosylation.

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Convergent Synthesis of the Nonreducing Hexasaccharide Fragment and the Dodecasaccharide Scaffold of Marine Lipopolysaccharide Axinelloside A

Zeng,

Zhang,

Zhu

et al. 2024

Chemistry A European J

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A convergent synthesis of the dodecasaccharide scaffold of axinelloside A was achieved through Au(I)‐catalyzed [6+6] glycosylation. The initially devised [3+1+2] assembly of the nonreducing hexasaccharide fragment was low‐yielding, whereas a convergent [3+3] glycosylation under Au(I) catalysis was proven feasible, allowing for a semi‐gram scale preparation of the wanted hexasaccharide. The requisite 1,2‐cis glycosidic bonds were forged in a highly stereoselective fashion by virtue of remote acetyl group participation, and judicious manipulation of protecting groups. The synthetic dodecasaccharide has been properly protected for the downstream elaboration toward its natural form.

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Total Synthesis and Stereochemistry Assignment of Nucleoside Antibiotic A‐94964

Cited by 7 publications

References 66 publications

Total Synthesis of Starfish Cyclic Steroid Glycosides. Part 3, Formal Total Synthesis of Luzonicosides A and D

Total Synthesis of Starfish Cyclic Steroid Glycosides. Part 3, Formal Total Synthesis of Luzonicosides A and D

Synthesis of the Reducing‐end Hexasaccharide Fragment of Marine Lipopolysaccharide Axinelloside A

Convergent Synthesis of the Nonreducing Hexasaccharide Fragment and the Dodecasaccharide Scaffold of Marine Lipopolysaccharide Axinelloside A

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