Die Totalsynthese von Solanesol

✍ Scribed by R. Rüegg; U. Gloor; A. Langemann; M. Kofler; C. von Planta; G. Ryser; O. Isler

• Publisher: John Wiley and Sons
• Year: 1960
• Tongue: German
• Weight: 446 KB
• Volume: 43
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19600430637

✦ Synopsis

Abstract

The structure of solanesol has been confirmed by total synthesis starting from trans‐geranylacetone. By six successive isoprenoid extensions via the tertiary acetylene carbinols, partial hydrogenation of the triple bond, transformation into the primary bromide and acetoacetic ester synthesis, the all‐trans‐C~43~ ketone has been obtained. This has been converted into the primary C~45~ bromide by the above procedure and then transformed into solanesol by treatment with potassium acetate and subsequent saponification.