Stereoselective Synthesis of Functionalized Spiro[4.5]decanes by Claisen Rearrangement of Bicyclic Dihydropyrans

Nakazaki, Atsuo; Miyamoto, Hiroshi; Henmi, Kazuki; Kobayashi, Susumu

doi:10.1055/s-2005-868520

Synlett

2005

DOI: 10.1055/s-2005-868520

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Stereoselective Synthesis of Functionalized Spiro[4.5]decanes by Claisen Rearrangement of Bicyclic Dihydropyrans

Atsuo Nakazaki¹,

Hiroshi Miyamoto²,

Kazuki Henmi³

et al.

Abstract: A functionalized spiro[4.5]decane framework was synthesized by the Claisen rearrangement of 4-substituted bicyclic dihydropyrans in a highly stereoselective fashion.

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Cited by 3 publications

References 7 publications

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Toward a Synthesis of Fawcettimine-Type Lycopodium Alkaloids: Stereocontrolled Synthesis of a Functionalized Azaspirocycle Precursor

2018

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The stereocontrolled synthesis of a new azaspirocycle precursor of the fawcettimine-type Lycopodium alkaloids is described. Our approach provides an efficient entry to the azaspirocycle via a cascade Wacker-allylation sequence followed by a highly stereoselective Claisen rearrangement. This azaspirocycle, bearing all of the requisite functionality with pivotal stereogenic centers, is considered to be a versatile precursor useful for the fawcettimine-type Lycopodium alkaloids.

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Toward a Synthesis of Fawcettimine-Type Lycopodium Alkaloids: Stereocontrolled Synthesis of a Functionalized Azaspirocycle Precursor

2018

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Stereocontrolled Total Synthesis of (−)-Gleenol Using Claisen Rearrangement of Sterically Congested Dihydropyran

Nakazaki¹,

Era²,

Kobayashi³

2008

Chemistry Letters

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A stereocontrolled total synthesis of enantiomerically pure (−)-gleenol using an improved substrate to construct the spiro[4.5]decane through Claisen rearrangement has been achieved. The most striking feature of this synthesis is that the rearrangement of sterically congested dihydropyran, bearing all requisite substituents with proper stereochemistry, afforded the fully functionalized spiro[4.5]decane in a single step.

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Total Synthesis of (.+-.)-Gleenol and (.+-.)-Axenol via a Functionalized Spiro[4.5]decane

Nakazaki

Era

Kobayashi

2007

CHEMICAL & PHARMACEUTICAL BULLETIN

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Stereoselective Synthesis of Functionalized Spiro[4.5]decanes by Claisen Rearrangement of Bicyclic Dihydropyrans

Abstract: A functionalized spiro[4.5]decane framework was synthesized by the Claisen rearrangement of 4-substituted bicyclic dihydropyrans in a highly stereoselective fashion.

Cited by 3 publications

References 7 publications

Toward a Synthesis of Fawcettimine-Type Lycopodium Alkaloids: Stereocontrolled Synthesis of a Functionalized Azaspirocycle Precursor

Toward a Synthesis of Fawcettimine-Type Lycopodium Alkaloids: Stereocontrolled Synthesis of a Functionalized Azaspirocycle Precursor

Stereocontrolled Total Synthesis of (−)-Gleenol Using Claisen Rearrangement of Sterically Congested Dihydropyran

Total Synthesis of (.+-.)-Gleenol and (.+-.)-Axenol via a Functionalized Spiro[4.5]decane

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