Total synthesis of (+/-)-alantrypinone by hetero Diels-Alder reaction.
An efficient total synthesis of (+/-)-alantrypinone 4 by hetero Diels-Alder reaction of a novel pyrazine diene 9 with either a functionalized 3-alkylideneoxindole or 3-methyleneoxindole itself is described. The Diels-Alder reactions provide both the desired regiochemistry and exo selectivity. An interesting anionic equilibration between alantrypinone 4 and its epimer 31 or between its ester analogues 23 and 24 has been demonstrated, and a mechanism has been proposed.
Chen
Zecheng
Z
Department of Chemistry, University of Rochester, Rochester, New York 14627, USA.
Fan
Junfa
J
Kende
Andrew S
AS
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D011799:Quinazolines / Q000138:chemical synthesis* / Q000737:chemistry; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013237:Stereoisomerism
D000470:Alkaloids; D007211:Indoles; D011799:Quinazolines; C115545:alantrypinone