Synthesis of the cyclohexan subunit of baconipyrones A and B from furan.
[figure: see text] The synthesis of the cyclohexan subunit of the siphonarlid metabolites baconipyrones A and B from furan is described. A key step included the alkylative ring opening of 7-oxanorbornenic sulfone 4 and oxidative desulfonylation of compound 8.
Arjona
O
O
Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense, 28040 Madrid, Spain. arjonao@eucmax.sim.ucm.es
Menchaca
R
R
Plumet
J
J
D000818:Animals; D003500:Cyclization; D003510:Cyclohexanes / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D008974:Mollusca / Q000737:chemistry; D011753:Pyrones / Q000138:chemical synthesis*; D013329:Structure-Activity Relationship; D013450:Sulfones / Q000737:chemistry
D003510:Cyclohexanes; D005663:Furans; D011753:Pyrones; D013450:Sulfones; C430470:baconipyrone A; C430469:baconipyrone B; C410203:baconipyrone C