title: Chemoenzymatic Total Syntheses of the Enantiomers of the Protoilludanes 8-Deoxydihydrotsugicoline and Radudiol.
abstract: Chemoenzymatic and stereoselective total syntheses of the non-natural enantiomeric forms of the recently isolated protoilludane natural products 8-deoxydihydrotsugicoline (1) and radudiol (2) (viz. ent-1 and ent-2, respectively) are reported. The key steps involve the Diels-Alder cycloaddition of cyclopent-2-en-1-one to the acetonide derived from enantiomerically pure and enzymatically derived cis-1,2-dihydrocatechol 3, elaboration of the resulting adduct to the tricyclic ketone 12, and a photochemically promoted rearrangement of this last compound to the octahydro-1H-cyclobuta[e]indenone 13.
authors: Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, ACT 2601, Australia.
authors: Ee Ling
authors: EL
authors: Chang
authors: Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, ACT 2601, Australia.
authors: Benoit
authors: B
authors: Bolte
authors: Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, ACT 2601, Australia.
authors: Ping
authors: P
authors: Lan
authors: Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, ACT 2601, Australia.
authors: Anthony C
authors: AC
authors: Willis
authors: Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, ACT 2601, Australia.
authors: Martin G
authors: MG
authors: Banwell
mesh_terms: D001688:Biological Products / Q000737:chemistry; D002396:Catechols / Q000138:chemical synthesis* / Q000737:chemistry; D061565:Cycloaddition Reaction; D007192:Indenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C000611324:8-deoxydihydrotsugicoline; D001688:Biological Products; D002396:Catechols; D007192:Indenes; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; C000611326:cis-1,2-dihydrocatechol; C000611327:octahydro-1H-cyclobuta(e)indenone; C506221:protoilludane; C000611325:radudiol