Tetrahedron p. 2465 - 2476 (1992)
Update date:2022-07-30
Topics:
Gijsen, Harrie J. M.
Wijnberg, Joannes B. P. A.
Stork, Gerrit A.
De Groot, Aede
De Waard, Maarten A.
Van Nistelrooy, Johannes G. M.
The monoalcohols (-)-globulol (2), (-)-epiglobulol (3), (-)-ledol (4), and (+)-viridiflorol (5) were synthesized from (+)-aromadendrene (1). The cis-fused alloaromandedrone (14), the key intermediate used in the synthesis of 4 and 5, was obtained from the trans-fused apoaromadendrone (13) via a selective protonation of the thermodynamic enol trimethylsilylether 15. After hydroxylation of the tertiary C11 of 13 with RuO4, (+)-spathulenol (6), (-)-allospathulenol (7), and the aromadendrane diols 8-11 could be prepared. Compounds 2-11 were tested for antifungal properties, but their activity was only moderate.
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