ABSTRACT
(+) and (-)-Dihydropinidine and (+)- and (-)-epidihydropinidine were synthesized from hydroxy esters 1 and 2 which had been prepared by yeast reduction of methyl (2-oxocyclohexyl)acetate. The enantiomeric excess at the C-1 positions of 1 and 2 were both determined as more than 99% ee.
Subject(s)
Acetates/chemistry , Cyclohexanones/chemistry , Piperidines/metabolism , Saccharomyces cerevisiae/metabolism , Acetates/metabolism , Cyclohexanones/metabolism , Molecular Structure , Oxidation-Reduction , Piperidines/chemistryABSTRACT
(R) and (S)-Aldehydes 2, which are intermediates for the synthesis of (5R) and (5S)-HETE, were respectively synthesized from the yeast-mediated reductive products, hydroxy ester 3 and cis-lactone 4, through Baeyer-Villiger oxidation with complete retention of enantiomeric excess.
Subject(s)
Hydroxyeicosatetraenoic Acids/chemical synthesis , Yeasts/metabolism , Aldehydes/chemistry , Aldehydes/metabolism , Biotransformation , Cyclopentanes/chemistry , Cyclopentanes/metabolism , Esters/chemistry , Esters/metabolism , Glycols/chemistry , Glycols/metabolism , Hydroxyeicosatetraenoic Acids/biosynthesis , Hydroxylation , Ketones/chemistry , Ketones/metabolism , Lactones/chemistry , Lactones/metabolism , Oxidation-Reduction , StereoisomerismABSTRACT
(1S,2S,5R,6S)-6-(3,4-Methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octan-1,2-diol ((+)-1-hydroxysamin 1) was synthesized, starting from olefin 8. Stereoselective alpha-hydroxylation was achieved after converting 8 to aldehyde 13. Resulting unstable alpha-hydroxy aldehyde 14 was then transformed to (+)-1-hydroxysamin (1). This is a new efficient synthetic route to 1,2-oxygenated 6-arylfurofuran lignans.