Identification of 2,3-dihydro-gamma-ionylideneethanol in Cercospora cruenta.
During our scrutiny of GC-EI-MS date for C15 alcohols as putative intermediates on the ABA biosynthetic pathway in Cercospora cruenta, a trace amount of 5-[2',2'-dimethyl-6'-methylene-1'-cyclohexyl]-3-methyl-4-penten-1-ol (2,3-dihydro-gamma-ionylideneethanol) was identified. Feeding experiments indicated that this compound was not an intermediate to ABA, but a catabolite that originated from gamma-ionylideneacetaldehyde. The stereochemistry of 2,3-dihydro-gamma-ionylideneethanol was deduced to be (3R,1'S) from a comparison with an authentic specimen prepared via baker's yeast asymmetric reduction.
Yamamoto
H
H
Faculty of Agriculture, Niigata University, Ikarashi, Japan. hirotaka@agr.niigata-u.ac.jp
Inomata
M
M
Uchiyama
T
T
Oritani
T
T
D000438:Alcohols / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D001203:Ascomycota / Q000737:chemistry*; D003470:Culture Media; D000431:Ethanol / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
C437405:2,3-dihydroionylideneethanol; D000438:Alcohols; D000447:Aldehydes; D003470:Culture Media; D000431:Ethanol