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Synthesis of the Dolabellane Diterpene Hydrocarbon (±)‐δ‐araneosene
Author(s) -
Jenny Luzi,
Borschberg HansJürg
Publication year - 1995
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19950780318
Subject(s) - diterpene , chemistry , geraniol , bicyclic molecule , yield (engineering) , hydrocarbon , stereochemistry , metabolite , organic chemistry , chromatography , essential oil , biochemistry , materials science , metallurgy
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 C AIN (Ascomycetes).