Volume 29, Issue 11
Natural Products
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ChemInform Abstract: Total Synthesis of (+)-3-Oxacarbacyclin. Part 2. Stereoselective Deprotonation and Completion of the Synthesis.

R. K. L. OSSENKAMP

R. K. L. OSSENKAMP

Inst. Org. Chem., RWTH Aachen, D-52074 Aachen, Germany

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H.-J. GAIS

H.-J. GAIS

Inst. Org. Chem., RWTH Aachen, D-52074 Aachen, Germany

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First published: 23 June 2010

Abstract

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ChemInform Abstract

The key steps in the synthesis of the title compound (X) are diastereoselective formation of the ester (I) described in the preceding paper, stereoselective deprotonation of the ketone (III) and stereoselective reduction of the keto group in compound (IX). This method can also be applied to prepare cicaprost, eptaloprost, and other side-chain modified 3-oxacarbacyclins.

chemical structure image

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