title: 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.
abstract: 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.
authors.affiliation: Department of Chemistry, University of York, Heslington, York, UKYO10 5DD. ijsf1@york.ac.uk
authors.forename: Ian J S
authors.initials: IJ
authors.lastname: Fairlamb
authors.forename: Stephanie
authors.initials: S
authors.lastname: Grant
authors.forename: Gideon
authors.initials: G
authors.lastname: Grogan
authors.forename: David A
authors.initials: DA
authors.lastname: Maddrell
authors.forename: Josephine C
authors.initials: JC
authors.lastname: Nichols
mesh_terms: 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
chemical_list: D001643:Bridged Bicyclo Compounds; D007783:Lactones; C472066:bicyclo(3,2,0)hept-2-en-6-one