Abstract

Recently, alkylation, alkenylation, and arylation of 4-cyclopentene-1,3-diol monoacetate have been published to produce 4-substituted-2-cyclopenten-1-ols (1,4- isomers) or 2-substituted-3-cyclopenten-1-ols (1,2-isomers). The product selectivity is usually high, and hence the products will provide a new access to the cyclopentanoids. This review describes scope and limitation of these reactions, synthetic advantages, comparison with the previous methods which also afford the same type of products indirectly or by using different substrates. In the latter part of this review, application of these reactions to synthesis of 12-oxo-PDA, OPC-8:0, Δ7-PGA1 methyl ester, the primary PG intermediates are presented.

Keywords: carbon nucleophiles, monoacetate, 4-cyclopentanoids, 4-substituted-2-cyclopenten-1-ols