Premium
Synthesis of Tricyclic Ketones with Sesquiterpene Skeletons by Acid‐Catalyzed Rearrangement of β ‐Monocyclofarnesol
Author(s) -
Fráter Georg,
Müller Urs,
Kraft Philip
Publication year - 1999
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/(sici)1522-2675(19990407)82:4<522::aid-hlca522>3.0.co;2-5
Subject(s) - chemistry , tricyclic , sesquiterpene , catalysis , terpene , hydrolysis , organic chemistry , ketone , wittig reaction , carroll rearrangement , acid catalysis , stereochemistry , claisen rearrangement
Starting from dihydro‐ β ‐ionone ( 6 ) a mixture of three tricyclic ketones with sesquiterpene skeletons 14 , 15 , and 16 was prepared by Wittig‐Horner reaction with triethyl phosphonoacetate, Red‐Al ® reduction, acid‐catalyzed rearrangement of the resulting β ‐monocyclofarnesol ( 7 ), alkaline hydrolysis of the formates 8 – 10 , and subsequent molybdenium‐catalyzed oxidation. The mechanistic background of the acid‐catalyzed rearrangement of β ‐monocyclofarnesol ( 7 ) is discussed in detail. The resulting tricyclic ketones 14 – 16 exhibit intense woody odor notes with peppery vetiver or camphoraceous cedarwood aspects.