Rh(I)-catalyzed ring opening of an IMDAF-derived oxabicyclo cycloadduct as the key step in the synthesis of (+/-)-epi-zephyranthine.
[reaction: see text] A new strategy for epi-zephyranthine has been developed that is based in part on an extraordinarily facile intramolecular Diels-Alder reaction of a 2-imido-substituted furan. By using a Rh(I)-catalyzed ring opening of the resulting oxabicyclic adduct, the cis-diol stereochemistry of epi-zephyranthine was established.
Wang
Qiu
Q
Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.
Padwa
Albert
A
D000470:Alkaloids / Q000737:chemistry; D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry; D002384:Catalysis; D005663:Furans / Q000737:chemistry; D007211:Indoles / Q000737:chemistry; D010617:Phenanthridines / Q000737:chemistry; D012238:Rhodium; D013237:Stereoisomerism
D000470:Alkaloids; D047151:Amaryllidaceae Alkaloids; D019086:Bridged Bicyclo Compounds, Heterocyclic; D005663:Furans; D007211:Indoles; D010617:Phenanthridines; C429964:hexahydroindolinone; C431927:zephyranthine; D012238:Rhodium