Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 497 - 517
Published: Jan. 1, 2024
Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(21), P. 14410 - 14415
Published: May 16, 2024
Strained cyclic tetrylones are important synthons due to various synthetic applications. Connecting two tetrylone rings through a single shared quaternary group 14 element atom form spirocyclic molecule has been unexplored both theoretically and experimentally. The formation of motif challenge. In contrast, the reaction amidinato disilicon(I) 1, (Me3P)2SiCl4, KC8 afforded π-delocalized spiro[3.3]heptasila-2,6-diylidone2 tetrasilacyclobutadiene byproducts 3 4. Compound 2 is smallest derivative, which composed σ-type lone pair delocalized π bond in each all-silicon ring. electronic property supported by its coordination with W(CO)5 moiety.
Language: Английский
Citations
7
Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(39), P. 21197 - 21202
Published: Sept. 21, 2023
In conceptual terms, the first total synthesis of cytotoxic marine natural product njaoamine C differs from all known approaches toward related alkaloids manzamine superfamily in that both macrocyclic rings enveloping diazatricyclic core are concomitantly formed; this goal was reached by double ring closing alkyne metathesis (dRCAM). The success maneuver does not merely reflect a favorable preorientation four chains need to be concatenated proper pairwise manner but is also outcome dynamic covalent chemistry involving error correction chosen "canopy" molybdenum alkylidyne catalyst. end game downstream dRCAM capitalizes on striking chemoselectivity palladium-catalyzed hydrostannation, which selects for (hetero)arylalkynes even presence sterically much more accessible dialkylalkynes or alkenes; preference, method complements classical repertoire hydrometalation and semireduction reactions.
Language: Английский
Citations
16
Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(22), P. 15420 - 15427
Published: May 20, 2024
We report the strain-induced [2 + 2] cycloadditions of cyclic allenes for assembly highly substituted cyclobutanes. By judicious choice trapping agent, complex scaffolds bearing heteroatoms, fused rings, contiguous stereocenters, spirocycles, and quaternary centers are ultimately accessible. Moreover, we show that resulting cycloadducts can undergo thermal isomerization. This study provides an alternative strategy to photochemical accessing functionalized cyclobutanes, while validating use underexplored strained intermediates architectures.
Language: Английский
Citations
5
Nature Synthesis, Journal Year: 2025, Volume and Issue: 4(4), P. 421 - 431
Published: April 9, 2025
Language: Английский
Citations
0
Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown
Published: April 9, 2024
The control of the selectivity is a central issue in total synthesis complex natural products. In this paper, we report (±)-keramaphidin B and (±)-ingenamine. key reaction DMAP-catalyzed Diels–Alder which regioselectivity completely controlled by dynamic crystallization. Our successfully demonstrates that crystallization can be an alternative when not either kinetic or thermodynamic approaches solution.
Language: Английский
Citations
3
Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(32)
Published: May 2, 2024
We describe a full account of our synthetic strategy leading to the first total synthesis manzamine alkaloid lissodendoric acid A . These efforts demonstrate that strained cyclic allenes are valuable building blocks and can be employed efficiently in synthesis.
Language: Английский
Citations
3
Organic Letters, Journal Year: 2024, Volume and Issue: 26(17), P. 3602 - 3606
Published: April 22, 2024
We report an experimental and computational investigation of the likely mechanism a cascade reaction. The reaction involves intramolecular Diels–Alder reaction, followed by C–C bond cleavage, to afford complex bridged bicyclic product. As multiple pathways could be envisioned for latter step, cleavage step was investigated. Two reasonable were evaluated. Both computations experiments indicate that proceeds retro-carbonyl-ene pathway rather than retro-aldol pathway. This underscores synergy between studies establishes interesting complexity-generating transformation.
Language: Английский
Citations
3
Organic Letters, Journal Year: 2024, Volume and Issue: 26(30), P. 6465 - 6470
Published: July 24, 2024
Reactions of α-pyrones with oxacyclic allenes in Diels–Alder trappings are described. We investigate regioselectivity trends and perform competition experiments to assess the influence structural electronic features on relative reaction rates. also demonstrate stereospecific trapping an allene, which proceeds high optical yield. This study provides insight into strained cyclic allene reactivity, as well new synthetic tools for rapid construction complex, heterocyclic scaffolds.
Language: Английский
Citations
1
Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(32)
Published: May 2, 2024
Abstract We describe a full account of our synthetic strategy leading to the first total synthesis manzamine alkaloid lissodendoric acid A . These efforts demonstrate that strained cyclic allenes are valuable building blocks and can be employed efficiently in synthesis.
Language: Английский
Citations
0
Progress in heterocyclic chemistry, Journal Year: 2024, Volume and Issue: unknown, P. 497 - 517
Published: Jan. 1, 2024
Citations
0