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1 article(s) from Kelch, André S

The preparation of several 1,2,3,4,5-functionalized cyclopentane derivatives

André S. Kelch,
Peter G. Jones,
Ina Dix and
Henning Hopf

Beilstein J. Org. Chem. 2013, 9, 1705–1712, doi:10.3762/bjoc.9.195

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Graphical Abstract

Scheme 1: The first members of the [n]radialene series and retrosynthesis for [5]radialene (3).

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Scheme 2: Preparation of cis,cis,cis,cis-1,2,3,4,5-pentakis(hydroxymethyl)cyclopentane (16) according to Tolb...

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Scheme 3: The preparation of derivatives of 16 better suited for nucleophilic substitution and elimination.

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Figure 1: Structure of 19 in the crystal; ellipsoids represent 50% probability levels.

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Scheme 4: Preparation of the pentaacetate 21 from 16.

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Scheme 5: Preparation of the cycloheptadiene octaesters 24/25 according to Diels [11] and Le Goff [13], respectively,...

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Figure 2: Structure of 24 in the crystal; ellipsoids represent 30% probability levels.

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Figure 3: Structure of 26 in the crystal; ellipsoids represent 30% probability levels.

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Scheme 6: Derivatives derived from the pentaester mixture 26/27.

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Scheme 7: Bromination of 1,2,3,4,5-pentamethylcyclopenta-1,3-diene (8).

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Figure 4: Structure of 32 in the crystal; ellipsoids represent 50% probability levels.

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Published 19 Aug 2013

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