Issue 7, 1990

The synthesis of novel benzomorphan analogues: a new intramolecular acid-catalysed aldol route to benzannelated bicyclo[3.3.1]nonane derivatives. X-Ray molecular structure of 8-hydroxy-1-methoxytricyclo[7.3.1.02,7]trideca-2,4,6-trien-10-one

Abstract

Novel benzomorphan analogues are described in which the piperidine ring is replaced by an aminocyclohexane ring. The key synthetic intermediate, benzannelated bicyclo[3.3.1]nonane derivative (12), is prepared by an efficient three-step synthetic route based on the addition of 2-lithiobenzaldehyde ethylene acetal to cyclohexane-1,4-dione monoethylene acetal followed by methylation, acid-catalysed deprotection, and in situ intramolecular aldol condensation. The stereospecificity of the aldol cyclisation to give intermediate (12) is noteworthy. Preliminary studies of the synthetic potential of the methodology for the preparation of derivatives with varying oxidation and substitution patterns are also described.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1990, 2145-2150

The synthesis of novel benzomorphan analogues: a new intramolecular acid-catalysed aldol route to benzannelated bicyclo[3.3.1]nonane derivatives. X-Ray molecular structure of 8-hydroxy-1-methoxytricyclo[7.3.1.02,7]trideca-2,4,6-trien-10-one

R. J. K. Taylor, S. M. Turner, D. C. Horwell, O. W. Howarth, M. F. Mahon and K. C. Molloy, J. Chem. Soc., Perkin Trans. 1, 1990, 2145 DOI: 10.1039/P19900002145

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