The enantioselective synthesis of elecanacin through an intramolecular naphthoquinone-vinyl ether photochemical cycloaddition.
Elecanacin, an unusual cyclobuta-fused naphthalene-1,4-dione derivative isolated from the bulbs of Eleutherine Americana Merr. et Heyne (Iridaceae) has been obtained, together with its epimer isoelecanacin, by a 2 + 2 cycloaddition resulting from irradiation of 5-methoxy-2-(2-vinyloxypropyl)naphthalene-1,4-dione. The synthesis of enantiopure elecanacin starting with (R)-propylene oxide has established the absolute configuration of the natural product and has revealed that the sample isolated from the bulbs possessed an enantiomeric excess of only 14%.
School of Biomedical, Biomolecular and Chemical Sciences, University of Western Australia, 35 Stirling Highway, Crawley, WA 6009, Australia.
Linda B
LB
Nielsen
Dieter
D
Wege
D001671:Biochemistry / Q000379:methods*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis / Q000737:chemistry*; D010777:Photochemistry / Q000379:methods*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
D009285:Naphthoquinones; D014753:Vinyl Compounds; C521642:elecanacin; C100195:vinyl ether