Although isolation of aciphyllene 1 was reported as early as 1983,
it was only in 2007 the first report appeared in the literature on the synthesis of aciphyllenes.
In 2007, research group of Pedro reported the semi-synthesis of theputative structure of aciphyllene, Scheme 1.
Enantiospecific synthesis of natural guaidienones 2 and 3, and their
diastereomer 4 has been accomplished starting from dihydrocarvone
via cyperone. Subsequent deoxygenation of guaiadienone 2 generated
1, whose NMR spectral data was found to differ with the aciphyllene
isolated from D. hirusta. Deoxygenation of guaidienone 3 generated 5,
whose NMR data was found to be identical to that of the natural aciphyllene
isolated from D. hirusta. Similarly, deoxygenation of the
guaiadienone