A short route to access oxaspiro[<i>n</i>,3,3]propellanes

Nassar, Youssef; Piva, Olivier

doi:10.1039/d0ob01169j

Cited by 6 publications

(2 citation statements)

References 29 publications

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“…Many synthetic attempts have been made for the synthesis of oxaspiro[n, 3,3]propellanes, but it was still a challenge for many researchers [144,145]. Nassar and Piva [146] in 2021 presented a valuable synthetic route toward the synthesis of oxaspiro[n, 3,3]propellane (317). The key steps involved hydroxymethylation (either photochemical or alternative routes consisting of three steps), metal-catalyzed cyclization and Simmons-Smith cyclopropanation.…”

Section: Synthesis Of Drugsmentioning

confidence: 99%

Simmons–Smith Cyclopropanation: A Multifaceted Synthetic Protocol toward the Synthesis of Natural Products and Drugs: A Review

Munir,

Zahoor,

Javed

et al. 2023

Molecules

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Simmons–Smith cyclopropanation is a widely used reaction in organic synthesis for stereospecific conversion of alkenes into cyclopropane. The utility of this reaction can be realized by the fact that the cyclopropane motif is a privileged synthetic intermediate and a core structural unit of many biologically active natural compounds such as terpenoids, alkaloids, nucleosides, amino acids, fatty acids, polyketides and drugs. The modified form of Simmons–Smith cyclopropanation involves the employment of Et2Zn and CH2I2 (Furukawa reagent) toward the total synthesis of a variety of structurally complex natural products that possess broad range of biological activities including anticancer, antimicrobial and antiviral activities. This review aims to provide an intriguing glimpse of the Furukawa-modified Simmons–Smith cyclopropanation, within the year range of 2005 to 2022.

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Section: Synthesis Of Drugsmentioning

confidence: 99%

Simmons–Smith Cyclopropanation: A Multifaceted Synthetic Protocol toward the Synthesis of Natural Products and Drugs: A Review

Munir,

Zahoor,

Javed

et al. 2023

Molecules

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“…[32][33][34] Moreover, we recently described access to propellane derivatives from easily available bicyclic hydroxylactones. 35,36 Herein, we report the synthesis of a new class of propellanes that contain a hexahydroindeno[2,1-c]pyran subunit by starting from unsaturated alcohols.…”

Section: Scheme 2 a Tandem Prins/friedel-crafts Reactionmentioning

confidence: 99%

Access to Hexahydroindeno[2,1-c]pyran-Based Propellanes by a Domino Prins/Friedel–Crafts Cyclization

Nassar¹,

Fache²,

Pelotier³

et al. 2022

Synthesis

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Synthesis of Angular Triquinane and [4.3.3]Propellane Derivatives via Ring‐Rearrangement Olefin Metathesis

2021

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Herein, a simple and useful approach to angular triquinane and [4.3.3]propellane moieties is described via olefin metathesis starting from exo and endo Diels‐Alder (DA) adducts containing norbornene unit. This approach involves DA reaction, and ring‐rearrangement metathesis (RRM) as key steps. Strained norbornene derivatives on allylation at bridgehead position(s) followed by ring‐opening metathesis and ring‐closing metathesis sequence delivered angular triquinane and also stereochemically different propellane derivatives.

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A short route to access oxaspiro[n,3,3]propellanes

Abstract: Novel access to oxaspiro[n,3,3]propellanes has been developed from bicyclic lactones directly prepared by a photochemical hydroxymethylation or alternatively by a three-step sequence. Thanks to the presence of additional hydroxy- and...

Cited by 6 publications

References 29 publications

Simmons–Smith Cyclopropanation: A Multifaceted Synthetic Protocol toward the Synthesis of Natural Products and Drugs: A Review

Simmons–Smith Cyclopropanation: A Multifaceted Synthetic Protocol toward the Synthesis of Natural Products and Drugs: A Review

Access to Hexahydroindeno[2,1-c]pyran-Based Propellanes by a Domino Prins/Friedel–Crafts Cyclization

Synthesis of Angular Triquinane and [4.3.3]Propellane Derivatives via Ring‐Rearrangement Olefin Metathesis

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