Abstract
The labile sesquiterpene hydrocarbon (−)-(1 R,7 S,10 R)-cadina-3,5-diene was isolated from manuka oil ( Leptospermum scoparium) by preparative gas chromatography, while its enantiomer is present in a chemotype of the liverwort Conocephalum conicum collected in southern Germany. The structure and absolute configuration was derived by NMR investigations, enantioselective gas chromatography and by conversion into a series of products of known stereochemistry by acid catalysed rearrangement, e.g. (−)-(7 S,10 R)- trans-calamenene, (−)-(7 S,10 R)-cadina-1(6),4,diene, (−)-(1 R,7 S,10 R)-bicyclosesquiphellandrene and (−)-(1 R,10 R)-zonarene. In addition, (+)-δ-amorphene was identified as a constituent of L. scoparium, while (−)-δ-amorphene is present in vetiver oil. Both enantiomers of this sesquiterpene, which has not been described as a natural product so far, were prepared by rearrangement of an enantiomeric mixture of germacrene D isolated from Solidago canadensis.
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