Synthesis of the dolabellane diterpene hydrocarbon (±)-δ-araneosene

Article abstract of DOI:10.1002/hlca.19950780318

The racemic form of the bicyclic diterpene hydrocarbon δ-araneosene (4), endowed with the dolabellane skeleton, was prepared from geraniol in two different ways. The more efficient route involved 13 steps and proceeded with an overall yield of 3.6% (average: 77% per step). With this reference sample at hand, the hitherto elusive metabolite (-)-4, a likely biogenetic precursor of cycloaraneosene ((-)-3) and sordaricin ((-)-1), could finally be isolated in ≥ 99.5% purity from the neutral fractions of the mold Sordaria araneosa CAIN (Ascomycetes).