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
Current Organic Chemistry
Title: Installation of Carbon Nucleophiles onto Monoacetate of 4-Cyclopentene- 1,3-diol and Synthesis of Cyclopentanoids
Volume: 7 Issue: 2
Author(s): Yuichi Kobayashi
Affiliation:
Keywords: carbon nucleophiles, monoacetate, 4-cyclopentanoids, 4-substituted-2-cyclopenten-1-ols
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.
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Cite this article as:
Kobayashi Yuichi, Installation of Carbon Nucleophiles onto Monoacetate of 4-Cyclopentene- 1,3-diol and Synthesis of Cyclopentanoids, Current Organic Chemistry 2003; 7 (2) . https://dx.doi.org/10.2174/1385272033373120
DOI https://dx.doi.org/10.2174/1385272033373120 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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