Volume 29, Issue 1
Natural Products
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ChemInform Abstract: Synthesis and Receptor Binding Affinity of Conformationally Restricted Retinoic Acid Analogues.

M. F. WONG

M. F. WONG

Div. Med. Chem. Pharmacogn., Coll. Pharm., Ohio State Univ., Columbus, OH 43210, USA

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J. J. REPA

J. J. REPA

Div. Med. Chem. Pharmacogn., Coll. Pharm., Ohio State Univ., Columbus, OH 43210, USA

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M. CLAGETT-DAME

M. CLAGETT-DAME

Div. Med. Chem. Pharmacogn., Coll. Pharm., Ohio State Univ., Columbus, OH 43210, USA

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R. W. JUN. CURLEY

R. W. JUN. CURLEY

Div. Med. Chem. Pharmacogn., Coll. Pharm., Ohio State Univ., Columbus, OH 43210, USA

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First published: 24 June 2010

Abstract

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ChemInform Abstract

Efforts to synthesize two conformationally restricted retinoids utilizing a cyclopropyl ring as bioisostere for the C9—C10 double bond are described. The attempted synthesis of the cis-isomer leads mainly to unidentified products and the unexpected epimerization to the trans-derivative (VII). The latter is synthesized independently starting from the cyclopropane (I).

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