Catalytic Asymmetric Synthesis of Benzobicyclo[3.2.1]octanes

Pasha, Mohammed Anif; Swamy, Peraka; Ramachary, Dhevalapally B.

doi:10.1002/chem.202100985

Cited by 10 publications

(1 citation statement)

References 48 publications

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“…One of its structural features is the unprecedented bicyclo[3.2.1]octane moiety derived from 2-hydroxy-1,4-naphthoquinone (lawsone), and it is the only known natural product containing such a structural motif. 7 Meanwhile, its cage-like structure with seven rings and six continuous stereocenters, including one all-carbon quaternary center, makes it an attractive, but challenging synthetic target. During the preparation of this manuscript, George and co-workers reported their elegant bio-inspired approach to peshawaraquinone ( 1 ) via dimerization of dehydro-α-lapachone.…”

Section: Introductionmentioning

confidence: 99%

Total synthesis of peshawaraquinone through late-stage [3 + 2] cycloaddition or α-ketol rearrangement

Guo,

Ren,

Sang

et al. 2024

Org. Chem. Front.

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Section: Introductionmentioning

confidence: 99%

Total synthesis of peshawaraquinone through late-stage [3 + 2] cycloaddition or α-ketol rearrangement

Guo,

Ren,

Sang

et al. 2024

Org. Chem. Front.

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Strategies for the Construction of Benzobicyclo[3.2.1]octane in Natural Product Synthesis

Liu,

Li,

Zhang

et al. 2024

Chemistry A European J

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Benzobicyclo[3.2.1]octane is a cage‐like unique motif containing a bicyclo[3.2.1]octane structure fused with at least one benzene ring. It is found in various natural products that exhibit structural complexities and important biological activities. The total synthesis of natural products possessing this challenging structure has received considerable attention, and great advances have been made in this field during the past 15 years. This review summarizes thus far achieved chemical syntheses and synthetic studies of natural compounds featuring the benzobicyclo[3.2.1]octane core. It focuses on strategic approaches constructing the bridged structure, aiming to provide a useful reference for inspiring further advancements in strategies and total syntheses of natural products with such a framework.

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Organocatalytic One‐Pot Synthesis of Pseudo‐Terpenoids

et al. 2022

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Structurally complex cedrane scaffolds were synthesized in very good yields with high chemo-and diastereoselectivities in a sequential one-pot manner. A combination of intermolecular olefination, intramolecular Michael and Michael reactions or intermolecular olefination, intramolecular Michael and aldol reactions were used as the key steps from the readily available hydroxy-p-quinone butanals and phosphoranes with catalytic amounts of quinine at ambient temperatures for a few hours. This is a unique one-pot combination of coupling and annulation routes for the green synthesis of a library of tricyclic pseudo-terpenoids (cedrane scaffolds) with high selectivity and yields. Organocatalytic ring isomerization was highlighted through transforming one ring into another one by retrocyclization. We have discussed thoroughly mechanistic aspects of these tandem coupling/annulation and ring isomerization reactions based on control experiments and X-ray crystal structure analysis.

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Catalytic Asymmetric Synthesis of Benzobicyclo[3.2.1]octanes

Cited by 10 publications

References 48 publications

Total synthesis of peshawaraquinone through late-stage [3 + 2] cycloaddition or α-ketol rearrangement

Total synthesis of peshawaraquinone through late-stage [3 + 2] cycloaddition or α-ketol rearrangement

Strategies for the Construction of Benzobicyclo[3.2.1]octane in Natural Product Synthesis

Organocatalytic One‐Pot Synthesis of Pseudo‐Terpenoids

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