Modellreaktionen zur Biosynthese von Verbindungen der Damascon-Reihe und ihre präparative Anwendung

✍ Scribed by Günther Ohloff; Valentin Rautenstrauch; Karl H. Schulte-Elte

• Publisher: John Wiley and Sons
• Year: 1973
• Tongue: German
• Weight: 762 KB
• Volume: 56
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19730560507

✦ Synopsis

Abstract

We report a new general synthesis of damascones. In the presence of acids, 7, 8‐dehydro‐β‐ionole (10) or the related diols 11 are converted into a mixture of β‐damascone (2) and the 7, 8‐dehydrotheaspiranes (19). In the same way the 6‐hydroxy‐7, 8‐dehydro‐α‐ionoles 12 are transformed into a mixture of β‐damascenone (3) and the 8‐oxatheaspiranes (20). The reaction Provides access to damascone derivatives 4–7 which have been found in nature.

These synthetic experiments lend support to our hypotheses concerning the biogenesis of damascones from suitable carotenoids or their metabolites.