Collect. Czech. Chem. Commun. 1990, 55, 1234-1242

Synthesis of optically active 1-(2-furyl)-3-pentanol. A simple route to (2S, 5R/S)-chalcogran

Eva Körblová, Bohumír Koutek, David Šaman, Aleš Svatoš, Petr Maloň and Miroslav Romaňuk

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


Enantioselective synthesis of the title alcohol VI is reported, which utilizes either pig pancreatic lipase mediated transesterification or a reduction with baker's yeast at the key steps. The transesterification of VI gives (S)-(+)-VI (e.e. 80%) or (R)-(-)-V (e.e. 50%), while the reduction of the corresponding α,β-unsaturated ketone IV affords (R)-(-)-VI (e.e. 30%). These intermediates allowed to prepare a mixture of chalcogran I diastereoisomers containing 54% of the biologically active (2S, 5R) isomer.