Issue 5, 1995

Synthesis of substructures of soraphen A: formation of the enolate of benzyl propionate

Abstract

During the preparation of substructures of the fungicidal natural product soraphen A 1, it was observed that the β-keto ester 12 was formed as the major product upon deprotonation of benzyl propionate with LDA. Studies of the stability of the enolate 13 showed that two mechanisms previously described for the decomposition of ester enolates cannot be operating in this example. A competition between deprotonation and condensation is proposed, which is in accord with the results described here and in the literature. The use of a reactive base is shown to provide good yields of the enolate 13. In addition, temperature is shown to be another factor influencing the yield of 13.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1995, 521-525

Synthesis of substructures of soraphen A: formation of the enolate of benzyl propionate

B. Loubinoux, J. Sinnes and A. C. O'Sullivan, J. Chem. Soc., Perkin Trans. 1, 1995, 521 DOI: 10.1039/P19950000521

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