Scandium Triflate Catalyzed Nazarov Cyclization of Arylvinyl Epoxides Derived from Alkoxides and Chloro(aryl)carbenes: A Facile Access to Resveratrol-Derived Natural Products

Satish, Nagam; Sudhakar, Gangarajula

doi:10.1055/s-0040-1705974

Synlett

2020

DOI: 10.1055/s-0040-1705974

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Scandium Triflate Catalyzed Nazarov Cyclization of Arylvinyl Epoxides Derived from Alkoxides and Chloro(aryl)carbenes: A Facile Access to Resveratrol-Derived Natural Products

Nagam Satish

Gangarajula Sudhakar

Abstract: The reaction of arylvinyl alkoxides with chloro(aryl)carbenes provided the corresponding arylvinyl epoxides that underwent Nazarov cyclization in a catalytic amount of scandium triflate, providing easy access to several highly substituted indenes, including some resveratrol-derived natural products.

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Cited by 4 publications

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Total Synthesis of Laurane and Guaiane Sesquiterpenoids via Oxidative Nazarov Reaction

Chen,

Zhang

et al. 2024

Chin. J. Chem.

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Comprehensive SummaryAs one of the most common structural motifs in natural products, cyclopentenones usually can be fabricated by Nazarov cyclization using divinyl ketones or functionalized tertiary divinyl carbinols (TDCs) as substrates. However, straightforward method for transforming unfunctionalized TDCs to their corresponding cyclopentenones is currently lacking. Herein, we wish to report the total syntheses of four structurally distinct terpenoids, namely laurane‐type marine sesquiterpenoids isolaurene, debromoaplysin and aplysin, and guaiane sesquiterpenoid guaiadienone A, all using a novel synthetic method, named oxidative Nazarov cyclization, as the key step. This work demonstrated our robust method is suitable for synthesizing various highly substituted cyclopentenones.

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Total Synthesis of Laurane and Guaiane Sesquiterpenoids via Oxidative Nazarov Reaction

Chen,

Zhang

et al. 2024

Chin. J. Chem.

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Transition Metal/Lewis Acid Catalyzed Reactions of Zerumbone for Diverse Molecular Motifs

Biji

Prabha

Lankalapalli

et al. 2021

The Chemical Record

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Zerumbone is a naturally occurring humulene type sesquiterpene, isolated from the rhizomes of Zingiber zerumbet (L.) Smith with excellent therapeutic potential and is recognized as a valuable synthon for the construction of diverse array of natural product motifs. In this review, we intended to highlight our achievements in utilizing abundant natural product zerumbone and its derivatives for the development of pharmacologically relevant molecular scaffolds. We provided an account of the transition‐metal catalyzed 1,4‐conjugate addition reactions of zerumbone and its derivatives along with palladium‐catalyzed cross‐couplings, transition metal‐based Lewis acid promoted interrupted Nazarov cyclisation reaction with substituted indoles and transannular cyclizations, photo‐induced transformations of zerumbone and its epoxide.

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Collective total synthesis of fusicoccane diterpenoids via Yu [5+2+1] cycloaddition and oxidative Nazarov cyclization

Xie,

Chen,

Zhang

et al. 2024

Cell Reports Physical Science

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Scandium Triflate Catalyzed Nazarov Cyclization of Arylvinyl Epoxides Derived from Alkoxides and Chloro(aryl)carbenes: A Facile Access to Resveratrol-Derived Natural Products

Cited by 4 publications

References 7 publications

Total Synthesis of Laurane and Guaiane Sesquiterpenoids via Oxidative Nazarov Reaction

Total Synthesis of Laurane and Guaiane Sesquiterpenoids via Oxidative Nazarov Reaction

Transition Metal/Lewis Acid Catalyzed Reactions of Zerumbone for Diverse Molecular Motifs

Collective total synthesis of fusicoccane diterpenoids via Yu [5+2+1] cycloaddition and oxidative Nazarov cyclization

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