Dictazoles: potential vinyl cyclobutane biosynthetic precursors to the dictazolines.
We report here the isolation of five new compounds, dictazoles A and B (1 and 2) and dictazolines C-E (5-7). Evidence is presented for the direct conversion of the cyclobutyl analogue 1 to its cyclohexyl constitutional isomer 5 via a vinyl cyclobutane rearrangement.
Dai
Jingqiu
J
Department of Chemistry, University of Hawaii at Manoa, Honolulu, Hawaii 96822, USA.
Jiménez
Jorge I
JI
Kelly
Michelle
M
Williams
Philip G
PG
D003432:Cross-Linking Reagents; D003503:Cyclobutanes / Q000737:chemistry*; D003510:Cyclohexanes / Q000737:chemistry*; D007093:Imidazoles / Q000737:chemistry*; D026121:Indole Alkaloids / Q000737:chemistry*; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013056:Spectrophotometry, Ultraviolet; D013141:Spiro Compounds / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
D003432:Cross-Linking Reagents; D003503:Cyclobutanes; D003510:Cyclohexanes; D007093:Imidazoles; D026121:Indole Alkaloids; D013141:Spiro Compounds; D014753:Vinyl Compounds; C550132:dictazole A; C550133:dictazole B; C550317:dictazoline C