Syntheses and chiroptical properties of C2-bissecocubane (tricyclo[4.2.0.03,6]octane) derivatives

Nakazaki, Masao; Naemura, Kōichirō; Sugano, Y.; Kataoka, Yasuto

doi:10.1021/jo01304a018

Cited by 10 publications

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“…D 3 -Trishomocubane ( 1 , C 11 H 14 ) is known to be a stable hydrocarbon with a planar chiral cage structure with a high degree of symmetry. , Its enhanced lipophilicity and propeller chirality combined with an extended cage size (5.5 Å) and a rigid architecture make it a worthwhile scaffold for further investigation. Several trishomocubane derivatives show improved pharmacokinetic properties as drugs, and they are also useful substrates for organocatalysis. − …”

Section: Introductionmentioning

confidence: 99%

Molecular Acrobatics in Polycyclic Frames: Synthesis of Functionalized D₃-Trishomocubanes via the Rearrangement Approach

Kotha

Cheekatla

2018

J. Org. Chem.

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A new synthetic route to D-trishomocubanone and oxa- D-trishomocubane derivatives has been established by the rearrangement approach. A remotely located methyl substituent in the six-membered ring contributed to the acid-catalyzed rearrangement of the cage dione in an unusual fashion. This rearrangement approach provided an attractive route to extended D-trishomocubanes, which are not accessible by the conventional multistep synthetic sequence. For the first time, two phenyl groups were incorporated from the solvent into the strained trishomocubane skeleton in an unprecedented manner via carbocation-mediated rearrangement with the aid of BF·OEt. Interestingly, an oxa-bridged trishomocubane skeleton was also formed during acid-promoted rearrangement.

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Section: Introductionmentioning

confidence: 99%

Molecular Acrobatics in Polycyclic Frames: Synthesis of Functionalized D₃-Trishomocubanes via the Rearrangement Approach

Kotha

Cheekatla

2018

J. Org. Chem.

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The Synthesis and Stereochemistry of Chiral Organic Molecules with High Symmetry

Nakazaki

1984

Topics in Stereochemistry

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Chiroptical Properties of Compounds ContainingCOGroups

Boiadjiev

Lightner

2009

Patai's Chemistry of Functional Groups

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Introduction The Octant Rule Compilation of Ketone and Aldehyde CD Unsaturated Ketones Compilation of Unsaturated Ketone and Aldehyde CD Exciton Chirality Addendum Acknowledgments

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Syntheses and chiroptical properties of C2-bissecocubane (tricyclo[4.2.0.03,6]octane) derivatives

Cited by 10 publications

References 1 publication

Molecular Acrobatics in Polycyclic Frames: Synthesis of Functionalized D₃-Trishomocubanes via the Rearrangement Approach

Molecular Acrobatics in Polycyclic Frames: Synthesis of Functionalized D₃-Trishomocubanes via the Rearrangement Approach

The Synthesis and Stereochemistry of Chiral Organic Molecules with High Symmetry

Chiroptical Properties of Compounds ContainingCOGroups

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Syntheses and chiroptical properties of C2-bissecocubane (tricyclo[4.2.0.03,6]octane) derivatives

Cited by 10 publications

References 1 publication

Molecular Acrobatics in Polycyclic Frames: Synthesis of Functionalized D3-Trishomocubanes via the Rearrangement Approach

Molecular Acrobatics in Polycyclic Frames: Synthesis of Functionalized D3-Trishomocubanes via the Rearrangement Approach

The Synthesis and Stereochemistry of Chiral Organic Molecules with High Symmetry

Chiroptical Properties of Compounds ContainingCOGroups

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Product

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Molecular Acrobatics in Polycyclic Frames: Synthesis of Functionalized D₃-Trishomocubanes via the Rearrangement Approach

Molecular Acrobatics in Polycyclic Frames: Synthesis of Functionalized D₃-Trishomocubanes via the Rearrangement Approach