Issue 2, 1976

Intramolecular condensation of steroidal α-acetoxy-ketones

Abstract

Intramolecular condensation of tertiary α-acetoxy-ketones in the cholestane series takes place in the presence of lithium di-isopropylamide to give products derived from nucleophilic attack of an ester enolate anion upon the adjacent oxo-group. When the acetoxy-group is axial, condensation proceeds rapidly at –78 °C to give the corresponding β-hydroxy-γ-lactone, but when it is equatorial the reaction is less efficient, and is attended by dehydration of the primary product.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1976, 212-219

Intramolecular condensation of steroidal α-acetoxy-ketones

J. R. Bull and A. Tuinman, J. Chem. Soc., Perkin Trans. 1, 1976, 212 DOI: 10.1039/P19760000212

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