25 research outputs found
Total Synthesis of Ginkgolide C and Formal Synthesis Ginkgolides A and B
Ginkgolides are diterpenes isolated from ginkgo biloba that exhibit strong PAF antagonistic activity as well as other interesting neuroprotective properties. These natural products possess a compact, highly oxygenated hexacyclic structure with two adjacent quaternary carbon centers, an unusual tert-butyl group, and up to twelve contiguous stereogenic carbon centers. The molecular architecture of ginkgolides, coupled with their remarkable biological profile, continues to be a source of fascination but also presents a formidable challenge for chemical synthesis. Herein, we reported the first total synthesis of ginkgolide C and the formal syntheses of ginkgolides A and B. The key to achieving these syntheses is a careful orchestration of carbon-carbon bond formation, guided by the compact nature of the ginkgolide structure
Modular Total Syntheses of Hyperforin, Papuaforins A, B, and C via Gold(I)-Catalyzed Carbocyclization
The
remarkable biological activities of polyprenylated polycyclic acylphloroglucinols
(PPAPs) combined with their highly oxygenated and densely functionalized
frameworks have stimulated the interest of synthetic organic chemists
over the past decade. Herein, we report the concise total syntheses
of four natural products PPAPs, of which some have antibacterial properties,
notably hyperforin and papuaforin A. The salient features of this
strategy are the short and gram-scalable synthesis of densely substituted
PPAPs scaffolds via a AuÂ(I)-catalyzed carbocyclization and the late-stage
functionalization for a unified access to a wide variety of PPAP
Modular Total Syntheses of Hyperforin, Papuaforins A, B, and C via Gold(I)-Catalyzed Carbocyclization
The
remarkable biological activities of polyprenylated polycyclic acylphloroglucinols
(PPAPs) combined with their highly oxygenated and densely functionalized
frameworks have stimulated the interest of synthetic organic chemists
over the past decade. Herein, we report the concise total syntheses
of four natural products PPAPs, of which some have antibacterial properties,
notably hyperforin and papuaforin A. The salient features of this
strategy are the short and gram-scalable synthesis of densely substituted
PPAPs scaffolds via a AuÂ(I)-catalyzed carbocyclization and the late-stage
functionalization for a unified access to a wide variety of PPAP
Modular Total Syntheses of Hyperforin, Papuaforins A, B, and C via Gold(I)-Catalyzed Carbocyclization
The
remarkable biological activities of polyprenylated polycyclic acylphloroglucinols
(PPAPs) combined with their highly oxygenated and densely functionalized
frameworks have stimulated the interest of synthetic organic chemists
over the past decade. Herein, we report the concise total syntheses
of four natural products PPAPs, of which some have antibacterial properties,
notably hyperforin and papuaforin A. The salient features of this
strategy are the short and gram-scalable synthesis of densely substituted
PPAPs scaffolds via a AuÂ(I)-catalyzed carbocyclization and the late-stage
functionalization for a unified access to a wide variety of PPAP
Modular Total Syntheses of Hyperforin, Papuaforins A, B, and C via Gold(I)-Catalyzed Carbocyclization
The
remarkable biological activities of polyprenylated polycyclic acylphloroglucinols
(PPAPs) combined with their highly oxygenated and densely functionalized
frameworks have stimulated the interest of synthetic organic chemists
over the past decade. Herein, we report the concise total syntheses
of four natural products PPAPs, of which some have antibacterial properties,
notably hyperforin and papuaforin A. The salient features of this
strategy are the short and gram-scalable synthesis of densely substituted
PPAPs scaffolds via a AuÂ(I)-catalyzed carbocyclization and the late-stage
functionalization for a unified access to a wide variety of PPAP
Modular Total Syntheses of Hyperforin, Papuaforins A, B, and C via Gold(I)-Catalyzed Carbocyclization
The
remarkable biological activities of polyprenylated polycyclic acylphloroglucinols
(PPAPs) combined with their highly oxygenated and densely functionalized
frameworks have stimulated the interest of synthetic organic chemists
over the past decade. Herein, we report the concise total syntheses
of four natural products PPAPs, of which some have antibacterial properties,
notably hyperforin and papuaforin A. The salient features of this
strategy are the short and gram-scalable synthesis of densely substituted
PPAPs scaffolds via a AuÂ(I)-catalyzed carbocyclization and the late-stage
functionalization for a unified access to a wide variety of PPAP
Modular Total Syntheses of Hyperforin, Papuaforins A, B, and C via Gold(I)-Catalyzed Carbocyclization
The
remarkable biological activities of polyprenylated polycyclic acylphloroglucinols
(PPAPs) combined with their highly oxygenated and densely functionalized
frameworks have stimulated the interest of synthetic organic chemists
over the past decade. Herein, we report the concise total syntheses
of four natural products PPAPs, of which some have antibacterial properties,
notably hyperforin and papuaforin A. The salient features of this
strategy are the short and gram-scalable synthesis of densely substituted
PPAPs scaffolds via a AuÂ(I)-catalyzed carbocyclization and the late-stage
functionalization for a unified access to a wide variety of PPAP
One-pot Diels–Alder cycloaddition/gold(I)-catalyzed 6-endo-dig cyclization for the synthesis of the complex bicyclo[3.3.1]alkenone framework
The rapid synthesis of bicyclo[m.n.1]alkanone cores possessing quaternary carbon centers adjacent to a bridged ketone represents a significant synthetic challenge. This type of architectural feature is embedded in various complex biologically active compounds such as hyperforin and garsubellin A. Herein, we report a highly diastereoselective one-pot Diels–Alder reaction/Au(I)-catalyzed carbocyclization to generate bicyclo[3.3.1]alkanones in yields ranging from 48–93%
Total Syntheses of Disorazoles A<sub>1</sub> and B<sub>1</sub> and Full Structural Elucidation of Disorazole B<sub>1</sub>
Described
herein are the first total syntheses of naturally occurring
antitumor agents disorazoles A<sub>1</sub> and B<sub>1</sub> and the
full structural assignment of the latter. The syntheses were achieved
through convergent strategies employing enantioselective constructions
of the required building blocks, including a novel Sharpless epoxidation/enzymatic
kinetic resolution of stannane-containing substrates that led selectively
to both enantiomeric forms of an epoxy vinyl stannane, and a series
of coupling reactions, including a Wittig reaction, a Suzuki coupling,
a Stille coupling, a Yamaguchi esterification and a Yamaguchi macrolactonization