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Synthesis 2012(5): 810-816  
DOI: 10.1055/s-0031-1289708
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

D 3-Trishomocubane-4-carboxylic Acid as a New Chiral Building Block: Synthesis and Absolute Configuration

Alexandr V. Gaidaia, Dmitriy M. Volochnyuk*b, Oleg V. Shishkinc, Andrey A. Fokina, Igor A. Levandovskiy*a, Tatyana E. Shubina*d
a Department of Organic Chemistry, Kiev Polytechnic Institute, Pr. Pobedy 37, 03056 Kiev, Ukraine
b Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska 5, Kiev-94, 02094, Ukraine
Fax: +38(44)5024832; e-Mail: D.Volochnyuk@enamine.net;
c Division of Functional Materials Chemistry, SSI ‘Institute for Single Crystals’, National Academy of Science of Ukraine, Lenina ave. 60, Kharkiv 61001, Ukraine
d Computer-Chemie-Centrum and Interdisciplinary Center for Molecular Materials, University Erlangen-Nuremberg, Nagelsbachstr. 25, 91052 Erlangen, Germany
Fax: +49(9131)8526565; e-Mail: tatyana.shubina@chemie.uni-erlangen.de;
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Publikationsverlauf

Received 22 November 2011
Publikationsdatum:
15. Februar 2012 (online)

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Abstract

The preparation of (±)-D 3-trishomocubanone on a multigram scale from 1,4-benzoquinone and cyclopentadiene was optimized to give the target product in 39% overall yield, that was transformed to (±)-D 3-trishomocubane-4-carboxylic acid via a three-step procedure involving the Corey-Chaykovsky reaction followed by boron trifluoride-diethyl ether catalyzed epoxide ring opening and further oxidation. Optically active (+)-D 3-trishomocubane-4-carboxylic acid was prepared through the resolution of the racemate by crystallization of its salt with (R)-phenylethylamine; the absolute configuration was assigned by X-ray crystal structure analysis.

Key words

D 3-trishomocubane - Corey-Chaykovsky reaction - absolute configuration - stereochemistry

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23

The final atomic coordinates, and crystallographic data for molecule (+)-18 have been deposited with the Cambridge Crystallographic Data Centre, 12 Union Road, CB2 1EZ, UK [fax: +44(1223)336033; e-mail: deposit@ccdc.cam.ac.uk, and are available on request quoting the deposition number CCDC 827046].