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Enantioselective Synthesis of the Unnatural Enantiomers of the Fungal Sesquiterpenoids Acorenone and Trichoacorenol
Author(s) -
Brock Nelson L.,
Dickschat Jeroen S.
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100688
Subject(s) - enantioselective synthesis , chemistry , enantiomer , stereochemistry , sesquiterpene , kinetic resolution , pulegone , metathesis , trichoderma , absolute configuration , polyketide , organic chemistry , botany , essential oil , chromatography , biosynthesis , biology , catalysis , polymer , polymerization , enzyme
Abstract The volatiles released by several strains of Trichoderma fungi were collected using a closed‐loop stripping apparatus and analysed by GC–MS. Most of the investigated strains released the two structurally related spirocyclic sesquiterpenoids trichoacorenol, previously identified in Trichoderma koningii (Huang et al., 1995), and acorenone. A new enantioselective synthesis of the enantiomer of the natural spirocyclic sesquiterpene acorenone and the first enantioselective synthesis of the related compound ent ‐trichoacorenol have been completed by a chiral‐pool approach starting from (+)‐( R )‐pulegone using ring‐closing metathesis as the key step. The absolute configuration of natural trichoacorenol from Trichoderma harzianum sp. 714 has been assigned by chiral GC–MS analysis and is the same as that in T. koningii .