A New Approach to Sesquiterpene Arenes of the 9,11-Drimenyl Type (= [(1E,2RS,4aRS,8aRS)-Octahydro-2,5,5,8a-tetramethylnaphthalen-1(2H)-ylidene] methyl Type)

✍ Scribed by Andreas Bernet; Karlheinz Seifert

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: German
• Weight: 195 KB
• Volume: 89
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200690071

✦ Synopsis

Abstract

A new reaction sequence for the synthesis of the sesquiterpene arenes (±)‐wiedendiol B ((±)‐1) and the siphonodictyal B derivative (±)‐ 21 consists in the coupling of (±)‐drimanoyl chloride ((±)‐3) with lithiated and appropriately substituted aromatic synthons to furnish the ketones (±)‐7 and (±)‐17 which were reduced to the benzyl alcohols (±)‐8a,b and (±)‐18a,b, respectively (Schemes 5, 4, and 12). The 9,11‐double bond of the drimenes (±)‐9 and (±)‐19 was formed by elimination of H~2~O from the benzyl alcohols (±)‐8a,b and (±)‐18a,b (Schemes 6 and 12). New alternatives were applied to this elimination reaction involving either the pyridine ⋅ SO~3~ complex or chloral as reagents.