title: Total synthesis of incarviditone and incarvilleatone.
abstract: The total synthesis of the racemic natural products (±)-incarviditone and (±)-incarvilleatone has been accomplished in three steps via biomimetic dimerization of (±)-rengyolone. Homochiral dimerization of (±)-rengyolone affords (±)-incarviditone through a domino oxa-Michael/Michael sequence. Heterochiral dimerization, involving a domino oxa-Michael/Michael/aldol reaction sequence, affords (±)-incarvilleatone. Single-crystal X-ray analysis of a derivative of (±)-incarviditone has resulted in revision of the originally proposed structure.
authors.affiliation: Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia.
authors.forename: Patrick D
authors.initials: PD
authors.lastname: Brown
authors.forename: Anthony C
authors.initials: AC
authors.lastname: Willis
authors.forename: Michael S
authors.initials: MS
authors.lastname: Sherburn
authors.forename: Andrew L
authors.initials: AL
authors.lastname: Lawrence
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D029402:Bignoniaceae / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D001572:Benzofurans; D005663:Furans; D006574:Heterocyclic Compounds, 2-Ring; D006576:Heterocyclic Compounds, 4 or More Rings; C509673:Rengyolone; C542670:incarviditone; C572693:incarvilleatone; C116609:3-hydroxybutanal