Synthesis of the Dolabellane Diterpene Hydrocarbon (±)‐δ‐araneosene | Zendy

Jenny Luzi | Zendy; Borschberg HansJürg | Zendy

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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).

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