title: Chemoenzymatic routes to enantiomerically enriched and polyoxygenated perhydro-3,5a-methanoindeno[4,5-c]furans related to the tashironin class of sesquiterpenes.
abstract: The alcohol 12, which is available in eight steps from the enzymatically derived cis-1,2-dihydrocatechol 8, engages in an intramolecular alkoxy radical-mediated remote functionalization reaction to form the tetrahydrofuran 13, thus establishing the perhydro-3,5a-methanoindeno[4,5-c]furan framework associated with the biologically active tashironins. Various manipulations of compound 13 and certain derivatives allow for the formation of compounds bearing strong structural resemblances to the title natural products.
authors: Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra ACT 2601, Australia.
authors: Mukesh K
authors: MK
authors: Sharma
authors: Martin G
authors: MG
authors: Banwell
authors: Anthony C
authors: AC
authors: Willis
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry*; D002396:Catechols / Q000138:chemical synthesis* / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D002396:Catechols; D005663:Furans; D012717:Sesquiterpenes; C000601930:perhydro-3,5a-methanoindeno(4,5-c)furan; C018674:tetrahydrofuran