Synthesis, Journal Year: 2023, Volume and Issue: 55(17), P. 2674 - 2682
Published: May 15, 2023
Abstract A protocol with available starting materials and mild conditions was developed for the synthesis of polysubstituted phenols functionalized carbocycles via acylation electron-poor alkenyl sulfoxides. The plausible mechanism investigated.
Language: Английский
Cell Reports Physical Science, Journal Year: 2024, Volume and Issue: 5(3), P. 101855 - 101855
Published: March 1, 2024
The fusicoccane diterpenoids have triggered particular interest from the organic synthesis community in recent years, owing to their promising biological profiles and complex chemical structures. Here, we report collective, asymmetric total syntheses of five diterpenoids, namely fusicoauritone, fusicogigantones A B, fusicogigantepoxide, anadensin. This work features a Yu [5+2+1] cycloaddition that is shown be swift approach access [5,8]-bicyclic ring system an oxidative Nazarov cyclization facilely fabricated critical cyclopentenone moiety via unfunctionalized tertiary divinyl carbinol (TDC) substrate. substrate scope study also revealed general robust transformation capable synthesizing highly substituted cyclopentenones TDCs.
Language: Английский
Citations
7
Advances in heterocyclic chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: Jan. 1, 2025
Language: Английский
Citations
0
Organic Letters, Journal Year: 2025, Volume and Issue: unknown
Published: Feb. 19, 2025
A synthetic route to the highly functionalized tetracyclic core framework of daphlongamine B is described. Key features strategy involve an oxidative dearomatization-induced [4+2] cycloaddition, a di-π-methane rearrangement, and ring-closing metathesis reaction. Our approach enables reliable construction fully elaborated precursor, which, in turn, provides valuable functional handles for further elaboration target molecule.
Language: Английский
Citations
0
Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown
Published: March 10, 2025
The family of Cephalotaxus diterpenoids represents a captivating class natural products that are significant interest from both structural and biological perspectives within our community. Here we wish to report 15-step, enantioselective total synthesis the diterpenoid fortalpinoid Q. Our approach highlights (1) Jacobsen's catalytic Claisen rearrangement enabled single-step formation two vicinal stereogenic centers, including an all-carbon quaternary center; (2) mild, oxoammonium salt (TEMPO+BF4-)-promoted dehydrative Nazarov cyclization swiftly forged crucial cyclopentadiene moiety via unfunctionalized tertiary divinyl carbinol (TDC) substrate; (3) facile aldol-lactonization cascade ultimately resolved last obstacle in synthesis.
Language: Английский
Citations
0
Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(1), P. 236 - 253
Published: Nov. 30, 2023
In this review, we elaborate and discuss the recent applications of straight-chain amino-α,β-unsaturated carbonyl compounds as versatile synthons in organocatalytic reactions for creation five- six-membered saturated nitrogen-containing heterocycles.
Language: Английский
Citations
10
European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(26)
Published: May 3, 2024
Abstract The Daphniphyllum alkaloids represent a particularly diverse class of complex diterpene alkaloids, which are characterized by their enormous structural diversity. daphnicyclidins, subgroup these stand out due to unique pentafulvene motif. This review article gives an overview the compounds that have been isolated so far and can be assigned this subgroup. Furthermore, all synthesis approaches total syntheses published date presented.
Language: Английский
Citations
2
The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(14), P. 10212 - 10222
Published: July 11, 2023
Hepta-2,3,5-trienedioates 1 have been employed as substrates to explore Lewis base-catalyzed annulation reactions. This leads the discovery of a phosphine-catalyzed [3+2] with electron-deficient alkenes for construction exocyclic olefinic cyclopentenes in good yields and moderate E:Z ratios under mild conditions. The is believed proceed tandem cyclization double bond migration which ε-ester crucial both processes. reaction also showcases substrate-controlled divergent reactivity compared that previous report.
Language: Английский
Citations
6
The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(21), P. 15151 - 15158
Published: Oct. 18, 2023
NHC-boranes have been treated as a reliable source of boryl radicals. In this study, regioselective hydroborylation ketene dithioacetals with NHC-borane was achieved under mild conditions via visible-light-promoted radical chain process using thiophenol proton donor and hydrogen atom transfer. This protocol features low-cost catalyst, good functional group tolerance, relatively broad range substrate scope, to excellent yields. Moreover, mechanism reaction preliminarily studied.
Language: Английский
Citations
4
Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(18), P. 5061 - 5066
Published: Jan. 1, 2024
A regioselective hydro trifluoromethylation of ketene dithioacetals with CF 3 SO 2 Na was achieved via a visible-light promoted radical-polar process under mild and operationally simple conditions, using an inexpensive organic photocatalyst.
Language: Английский
Citations
1
Organic Letters, Journal Year: 2022, Volume and Issue: 24(51), P. 9520 - 9524
Published: Dec. 16, 2022
The [7–5–5] tricyclic core of daphniphyllum alkaloids, containing contiguous stereogenic centers at C14 and C15 a tetrasubstituted alkene moiety between C9 C10, was constructed via cascade reaction that involved an electrocyclic pentadienyl cation intramolecular interception the resultant cyclopentenyl cation.
Language: Английский
Citations
2