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Functionalisation of saturated hydrocarbons. Part XI . Oxidation of cedrol, β‐ and γ‐eudesmol, sclareol, manoyl oxide, 1,9‐dideoxyforskolin, methyl trans ‐dihydroiasmonate, and tetrahydrolinalool by the ‘ Gif system’
Author(s) -
Barton Derek H. R.,
Beloeil JeanClauude,
Billion Annick,
Boivin Jean,
Lallemand JeanYves,
Lelandais Patrick,
Mergui Simone
Publication year - 1987
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.19870700824
Subject(s) - chemistry , terpenoid , stereochemistry , oxide , organic chemistry
The oxidation of cedrol ( 1 ), β‐ and γ‐eudesmol ( 6 and 7 , resp.), sclareol ( 14 ) manoyl oxide ( 15 ), 1,9‐dideoxyforskolin ( 22 ) (±)‐methyl trans ‐dihydrojasmonate ( 28 ), and tetrahydrolinalool ( 32 ) nearly all of natural terpenoid origin, by the ‘ Gif system’ has afforded a number of novel products ( 3 , 11 , and 12 , 16/17 , 18/19 , 26 , 29–31 , and ketones corresponding to 34–35 , res.). The structures of these compounds were established by spectroscopic techniques including 2D‐NMR and, where appropriate, by comparison with authentic samples.