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Secondary Metabolites by Chemical Screening, 28. Aspinonene, a New Multifunctional Fungal Metabolite
Author(s) -
Fuchser Jens,
Grabley Susanne,
Noltemeyer Mathias,
Philipps Siegrid,
Thiericke Ralf,
Zeeck Axel
Publication year - 1994
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199419940812
Subject(s) - chemistry , metabolite , acylation , epoxide , secondary metabolite , ketone , silylation , chirality (physics) , organic chemistry , stereochemistry , biochemistry , catalysis , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , gene , quark
A new C 9 epoxide named aspinonene ( 1 ) was found by chemical screening in the culture broth of Aspergillus ochraceus (strain FH‐A 6692). Its structure was deduced from spectroscopic data as well as from an X‐ray analysis of the dibromobenzoate of 1 . The configuration of C‐2 was further verified by esterification of the ketone 4 with chiral acids (Helmchen's method). The reactivity of the functional groups was studied by acylation, silylation, ketalization, and oxidation. Due to the diversity of its functional groups and the neighbouring centres of chirality 1 is discussed as a secondary metabolite suited as a building block for synthesis.