Collins, Dwight O.; Reynolds, Williams F.; Reese, Paul B.
Author Affiliation, Ana.
Department of Chemistry
Aromadendrane transformations by Curvularia lunata ATCC 12017
Date of Publication
The naturally occurring sesquiterpene squamulosone (1), isolated from Hyptis verticillata (Labiatae), was synthetically reduced to five analogues that were identified as (IS,10S)-9alpha-hydroxy-allo-aromadendrane (2). (1R, 10R)-9beta-hydroxyaromadendrane (3), (1S,10S)-allo-aromadendean-9-one (4), (1R,10R)-aromadendran-9-one (5) and aromadendra-1,9-diene (6). Each congener was incubated with the fungus Curvularia lunata ATCC 12017 in two different growth media. All the substrates except the deoxy compound 6 underwent a simple redox reaction. Ketone 5 additionally experienced remote hydroxylation while analogue 6, possessing a conjugated diene system, was most extensively metabolised. The substrates and products presented here, but one, are all novel.....