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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 14
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Original Articles

Synthesis of α‐Hydroxy Ketones from Terpene Aldehydes

Martin Schueler University of St Andrews, North Haugh, St Andrews, Scotland
,
Holger Zorn Institute of Food Chemistry, University of Hannover, Wunstorfer Str. 14, Hannover, D‐30453, Germany
,
Alexandra M. Z. Slawin University of St Andrews, North Haugh, St Andrews, Scotland
&
Ralf G. Berger Institute of Food Chemistry, University of Hannover, Wunstorfer Str. 14, Hannover, D‐30453, GermanyCorrespondence[email protected]
Pages 2591-2600 | Received 23 Feb 2004, Published online: 10 Jan 2011
 
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Abstract

Unsymmetrically substituted α‐hydroxy ketones possessing isoprenoid units within the molecule were synthesised from commercially available terpene aldehydes. The synthesis was applicable to α,β‐unsaturated aldehydes and afforded the respective α‐hydroxy‐methyl ketones in overall good yield. Tautomerisation of these products did not occur under the conditions of reaction but was observed upon heating. Diastereoisomeric α‐hydroxy ketones have been resolved, and X‐ray analysis on one of these analogues allowed for the elucidation of the stereochemistry after conversion into its camphanate ester.

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