Expeditious total syntheses of natural allenic products via aromatic ring umpolung.
Concise diastereoselective syntheses of the marine (+/-)-panacene and terrestrial (+/-)-desbromopanacene have been achieved in a few steps based on a concept of "aromatic ring umpolung". The synthetic avenue to the (+/-)-panacene involved a novel oxymercuration strategy to produce the correct configuration of the bromoallene moiety.
Sabot
Cyrille
C
Laboratoire de Méthodologie et Synthèse de Produits Naturels, Université du Québec à Montréal, C.P. 8888, Succ. Centre-Ville, Montréal, H3C 3P8 Québec, Canada.
Bérard
Didier
D
Canesi
Sylvain
S
D000466:Alkadienes / Q000737:chemistry*; D001572:Benzofurans / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000737:chemistry; D015394:Molecular Structure
D000466:Alkadienes; D001572:Benzofurans; D001688:Biological Products; D005663:Furans; C025947:propadiene; C039281:furan