A one-pot remote allylic hydroxylation and Baeyer-Villiger oxidation of a bicyclo[3.2.0]hept-2-en-6-one by Cunninghamella echinulata NRRL 3655.
7-exo-Methyl-7-endo-phenylbicyclo[3.2.0]hept-2-en-6-one 3 undergoes Baeyer-Villiger and allylic oxidation, to yield novel hydroxylactone 8 in good yield by Cunninghamella echinulata NRRL 3655, representing a one step biocatalytic access to a cyclopentanoid scaffold with three chiral centers. Interesting, allylic oxidation occurs with transposition of the double bond.
Fairlamb
Ian J S
IJ
Department of Chemistry, University of York, Heslington, York, UKYO10 5DD. ijsf1@york.ac.uk
Grant
Stephanie
S
Grogan
Gideon
G
Maddrell
David A
DA
Nichols
Josephine C
JC
D001643:Bridged Bicyclo Compounds / Q000737:chemistry* / Q000378:metabolism*; D002849:Chromatography, Gas; D020093:Cunninghamella / Q000737:chemistry* / Q000378:metabolism*; D006900:Hydroxylation; D007783:Lactones / Q000737:chemistry / Q000378:metabolism; D015394:Molecular Structure; D010084:Oxidation-Reduction
D001643:Bridged Bicyclo Compounds; D007783:Lactones; C472066:bicyclo(3,2,0)hept-2-en-6-one