Enzyme-controlled reactions giving alkanols of use in the synthesis of biologically active molecules.
(+/-)-Bicyclo[3.2.0]hept-2-en-6-one was reduced using a variety of fungi including yeasts. Baker's yeast gave 6-exo-(1R,5S,6S)-bicyclo[3.2.0]hept-2-en-6-ol and 6-endo-(1S,5R,6S)-bicyclo[3.2.0]hept-2-en-6-ol while Curvularia lunata and Mortierella ramanniana gave only the 6-endo-alcohol and optically active bicycloheptenone. The optically active bicycloheptenols were used to prepare prostaglandin F2 alpha in the natural configuration.
D000438:Alcohols; D001643:Bridged Bicyclo Compounds; D001952:Bridged-Ring Compounds; D055598:Chemical Phenomena; D002621:Chemistry; D003500:Cyclization; D015237:Dinoprost; D004798:Enzymes; D005658:Fungi / Q000378:metabolism; D003904:Mitosporic Fungi / Q000378:metabolism; D009090:Mucorales / Q000378:metabolism; D011460:Prostaglandins F / Q000096:biosynthesis; D012441:Saccharomyces cerevisiae / Q000378:metabolism; D013237:Stereoisomerism; D015003:Yeasts / Q000201:enzymology
D000438:Alcohols; D001643:Bridged Bicyclo Compounds; D001952:Bridged-Ring Compounds; D004798:Enzymes; D011460:Prostaglandins F; D015237:Dinoprost