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Synthesis of rac ‐Presilphiperfolan‐9‐ol
Author(s) -
Weyerstahl Peter,
Marschall Helga,
Schulze Matthias,
Schwope Ina
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619960526
Subject(s) - epimer , chemistry , odor , stereochemistry , terpene , organic chemistry
rac ‐Presilphiperfolan‐9‐ol ( 2 ) and three of its epimers ( 24, 29, 30 ) were synthesized by starting from the known 8‐hydroxy‐3,3,5‐trimethylbicyclo[3.3.0]octan‐2‐one ( 10 ). The spectroscopic data of rac ‐ 2 are identical with those of the natural (‐)‐presilphiperfolan‐9‐ol, previously isolated from Artemisia laciniata. rac ‐ 2 has a strong woody, amber odor whereas the 9‐epimer 24 smells strongly patchouli‐like.