Skeletal diversification by C–C cleavage to access bicyclic frameworks from a common tricyclooctane intermediate

Bakanas, Ian; Tang, Jess C; Sarpong, Richmond

doi:10.1039/d3cc00945a

Cited by 3 publications

(1 citation statement)

References 43 publications

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“…Sarpong and co-workers reported a skeletal editing of cycloadduct 169 via Lewis acidmediated selective ring opening. 144 Mykhailiuk and co-workers reported a unique synthesis of 3-aza BCHeps 173 via the reduction of spirocyclic oxetanyl nitriles 172 followed by cyclization. 145 Silverman and co-workers reported an asymmetric synthesis of functionalized BCHep 175 by intramolecular Mannich reaction utilizing a chiral sulfinamide.…”

Section: Template For Synthesis Thiemementioning

confidence: 99%

Recent Progress in Accessing Multi-functionalized Caged Hydrocarbons: En Route to Highly Functionalized Saturated (Bio)isosteres of Benzene Rings

Nagasawa,

Iwabuchi

2024

Synthesis

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Recently, many saturated bioisosteres of benzene ring have been developed, and their application in drug development has been evaluated. Most of these are caged hydrocarbons, which have rigid skeletons and three-dimensional spaces. Recent efforts to synthesize these caged hydrocarbons have enabled access to multi-functionalized congeners that are expected to be (bio)isosteres of multi-functionalized benzenes. This review article summarizes recently reported methods to obtain multi-functionalized (typically more than disubstituted) caged hydrocarbons.

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Section: Template For Synthesis Thiemementioning

confidence: 99%

Recent Progress in Accessing Multi-functionalized Caged Hydrocarbons: En Route to Highly Functionalized Saturated (Bio)isosteres of Benzene Rings

Nagasawa,

Iwabuchi

2024

Synthesis

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Photochemical Action Plots Reveal Red‐shifted Wavelength‐dependent Photoproduct Distributions

Carroll,

Pashley‐Johnson,

Frisch

et al. 2024

Chemistry A European J

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Photochemical action plots are a powerful tool for mapping photochemical reaction outcomes wavelength‐by‐wavelength. Typically, they map either the depletion of a reactant or the formation of a specific product as a function of wavelength. Herein, we exploit action plots to simultaneously map the formation of several photochemical products from a single chromophore. We demonstrate that the wavelength‐resolved mapping of two reaction products formed during the irradiation of a chalcone species not only shows wavelength dependence – exhibiting the typical strong red‐shift of the photochemical reactivity compared to the absorbance spectrum of the chromophore – but also a strong wavelength selectivity with remarkably different product distributions resulting from different irradiation wavelengths.

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Unique Reactivity of the 1,4‐Bis(silyloxy)‐1,3‐cyclopentadiene Moiety: Application to the Synthesis of 7‐Norbornanone Derivatives

Ikeuchi,

Hirokawa,

Sasage

et al. 2024

Chemistry A European J

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We describe a method for the synthesis of various 2‐silyloxy‐2‐norbornen‐7‐ones that exploits the specific reactivity of the 1,4‐bis(silyloxy)‐1,3‐cyclopentadiene framework, which is generated under silylating reaction conditions from a 2,2‐disubstituted‐1,3‐cyclopentanedione bearing the picolinoyloxy group at the 2' position of its C‐2 side chain. Our reaction system generates a carbocation via the release of the acyloxy group, forms a 4,5‐cis‐fused ring skeleton via the intramolecular attack at the resulting carbocation by a silyloxy‐substituted carbon in the 1,4‐bis(silyloxy)‐1,3‐cyclopentadiene moiety, and induces the skeletal rearrangement of the bicyclic core. This novel transformation of a 1,3‐cyclopentanedione moiety can be developed for the synthesis of other bicyclic frameworks fused to cyclopentenones.

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Skeletal diversification by C–C cleavage to access bicyclic frameworks from a common tricyclooctane intermediate

Abstract: Herein, the diversification of tricyclo[3.2.1.03,6]octane scaffolds to afford diverse bicyclic scaffolds is described. The strained tricyclooctanes are prepared in two steps featuring a blue light-mediated [2+2] cycloaddition. Strategies for the...

Cited by 3 publications

References 43 publications

Recent Progress in Accessing Multi-functionalized Caged Hydrocarbons: En Route to Highly Functionalized Saturated (Bio)isosteres of Benzene Rings

Recent Progress in Accessing Multi-functionalized Caged Hydrocarbons: En Route to Highly Functionalized Saturated (Bio)isosteres of Benzene Rings

Photochemical Action Plots Reveal Red‐shifted Wavelength‐dependent Photoproduct Distributions

Unique Reactivity of the 1,4‐Bis(silyloxy)‐1,3‐cyclopentadiene Moiety: Application to the Synthesis of 7‐Norbornanone Derivatives

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