Issue 8, 1998

Convenient synthesis of substituted cyclopentenones via [3 + 2] annulation of allylidenetriphenylphosphorane with 1,2-diacylethylenes: application to synthesis of (±)-methyl dehydrojasmonate

Abstract

(3-Alkoxycarbonyl-2-ethoxyprop-2-enylidene)triphenylphosphoranes 1 and 2 undergo [3 + 2] annulation with 1,2-diacylethylenes 3 to give 2-ethoxycyclopentadienes 6 as mixtures of the 1,3- and 1,4-diene. The mixtures are conveniently converted upon mild acid treatment into cyclopentenones 7 in a single form. Annulation of phosphorane 1 with acylmethylenemalonates 10 affords cyclopenta-1,3-dienes 11 in a highly regioselective fashion, which are readily converted into substituted cyclopentenones 12 in excellent yields. Phosphorane 1 also undergoes annulation with 1,2-acylacetylene 14 to give the fulvene 15, which is transformed into the exomethylenecyclopentenone 16. Furthermore, an application of the annulation to the synthesis of (±)-methyl dehydrojasmonate is described.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1998, 1389-1396

Convenient synthesis of substituted cyclopentenones via [3 + 2] annulation of allylidenetriphenylphosphorane with 1,2-diacylethylenes: application to synthesis of (±)-methyl dehydrojasmonate

Y. Himeda, Y. Tanaka, I. Ueda and M. Hatanaka, J. Chem. Soc., Perkin Trans. 1, 1998, 1389 DOI: 10.1039/A709296B

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements