Organic Letters, Год журнала: 2022, Номер 24(51), С. 9520 - 9524
Опубликована: Дек. 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.
Язык: Английский
Journal of the American Chemical Society, Год журнала: 2023, Номер 145(20), С. 10998 - 11004
Опубликована: Май 11, 2023
The first total synthesis of (±)- and (-)-daphnillonin B, a daphnicyclidin-type alkaloid with new [7-6-5-7-5-5] A/B/C/D/E/F hexacyclic core, has been achieved. [6-5-7] B/C/D ring system was efficiently diastereoselectively constructed via mild type I intramolecular [5+2] cycloaddition, followed by Grubbs II catalyst-catalyzed radical cyclization. [5-5] fused E/F synthesized diastereoselective Pauson-Khand reaction. Notably, the synthetically challenging core reassembled unique Wagner-Meerwein-type rearrangement from [6-6-5-7-5-5] framework found in calyciphylline A-type Daphniphyllum alkaloids.
Язык: Английский
Процитировано
25
Journal of the American Chemical Society, Год журнала: 2024, Номер 146(2), С. 1262 - 1268
Опубликована: Янв. 5, 2024
A concise enantioselective total synthesis of (−)-daphenylline, a hexacyclic Daphniphyllum alkaloid with unique benzene ring, was achieved in 14 steps. The commences two chiral stereocenters, C2 and C18, readily installed via Carreira's Ir/amine dual-catalyzed allylation. allylic bridgehead amine 6 rapidly prepared through Wickens' photoredox-catalyzed hydrocarboxylation olefin CuBr2-catalyzed α-amination ketone. tetracycle 4 formed Pd-catalyzed reductive Heck reaction or, more concisely, by Krische's Rh-catalyzed 1,6-enyne cyclization. In this synthesis, newly reported used twice, Friedel–Crafts acylation thrice.
Язык: Английский
Процитировано
11
RSC Advances, Год журнала: 2025, Номер 15(6), С. 4496 - 4525
Опубликована: Янв. 1, 2025
This review covers recent advancements in Diels–Alder reaction chemistry for total synthesis of Natural Products (2020–2023) and, where relevant, discusses key structural features and biological activity bioactive natural products.
Язык: Английский
Процитировано
1
Journal of the American Chemical Society, Год журнала: 2023, Номер 145(49), С. 27160 - 27166
Опубликована: Ноя. 28, 2023
The first and asymmetric total syntheses of rhodomollins A B, two rhodomollane type grayanoids featuring a d-homograyanane carbon skeleton an oxa-bicyclo[3.2.1] core, were accomplished via convergent strategy. Stille coupling lithium-halogen exchange/intramolecular nucleophilic addition to the aldehyde sequence employed assemble enantioenriched fragments. core was achieved through intramolecular SN2 substitution cyclic sulfate 1,2-diols (Williamson ether synthesis). ring oxidation states adjusted by Payne/Meinwald rearrangement subsequent redox transformations.
Язык: Английский
Процитировано
16
Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(23)
Опубликована: Март 30, 2023
The daphnezomine A-type subfamily of Daphniphyllum alkaloids structurally features a unique aza-adamantane core skeleton and anticipates efficient strategies for completing their syntheses to thoroughly investigate biological activities. Herein, divergent total (-)-daphnezomines A B (+)-dapholdhamine have been accomplished in 16-20 steps from known epoxide via rapid construction common intermediate. present work Ti-mediated radical cyclization establish the azabicyclo[3.3.1]nonane ring system, an intramolecular Heck reaction install bridgehead all-carbon quaternary stereocenter, tandem deprotection/reduction/keto amine-carbinolamine tautomerization furnish backbone, NIS-promoted 6-endo-trig aminocyclization assemble backbone.
Язык: Английский
Процитировано
15
Nature Communications, Год журнала: 2024, Номер 15(1)
Опубликована: Июль 13, 2024
The development of new antibiotics continues to pose challenges, particularly considering the growing threat multidrug-resistant Staphylococcus aureus. Structurally diverse natural products provide a promising source antibiotics. Herein, we outline concise approach for collective asymmetric total synthesis polycyclic xanthene myrtucommulone D and five related congeners. strategy involves rapid assembly challenging benzopyrano[2,3-a]xanthene core, highly diastereoselective establishment three contiguous stereocenters through retro-hemiketalization/double Michael cascade reaction, Mitsunobu-mediated chiral resolution with high optical purity broad substrate scope. Quantum mechanical calculations insight into stereoselective construction mechanism stereocenters. Additionally, this work leads discovery an antibacterial agent against both drug-sensitive drug-resistant S. This compound operates unique that promotes bacterial autolysis by activating two-component sensory histidine kinase WalK. Our research holds potential future drug development.
Язык: Английский
Процитировано
6
Chinese Chemical Letters, Год журнала: 2023, Номер 35(6), С. 109229 - 109229
Опубликована: Окт. 24, 2023
Язык: Английский
Процитировано
11
Journal of the American Chemical Society, Год журнала: 2024, Номер unknown
Опубликована: Ноя. 20, 2024
In this report, we detail two distinct synthetic approaches to calyciphylline A-type
Язык: Английский
Процитировано
4
Organic Letters, Год журнала: 2025, Номер unknown
Опубликована: Фев. 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.
Язык: Английский
Процитировано
0
Chinese Journal of Organic Chemistry, Год журнала: 2025, Номер 45(3), С. 866 - 866
Опубликована: Янв. 1, 2025
Язык: Английский
Процитировано
0