Issue 23, 1997

Control of stereochemistry in an intramolecular Diels–Alder reaction by the phenylsulfonyl group; an improved synthesis of pisiferol

Abstract

Thermolysis of 4a (X = H) gives 6a and 6b (X = H) in a ratio of 1∶4 whereas 4b (X = SO2Ph) gives more of the trans-ring junction product 6a (X = SO2Ph) suitable for the synthesis of pisiferol [ratio 6a∶6b (X = SO2Ph) = 1.5∶1]. Base catalysed elimination of the phenylsulfonyl group from 6a (X = SO2Ph) gives 18 which is hydrogenated to 6a (X = H), an intermediate in the synthesis of pisiferol. Both 6a and 6b (X = SO2Ph) have ring B in a half-boat conformation.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1997, 3531-3536

Control of stereochemistry in an intramolecular Diels–Alder reaction by the phenylsulfonyl group; an improved synthesis of pisiferol

E. J. Bush and D. W. Jones, J. Chem. Soc., Perkin Trans. 1, 1997, 3531 DOI: 10.1039/A702761C

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