Reactive enols in synthesis 2. Synthesis of (+)-latifolic acid and (+)-latifoline.
We describe a short, enantioselective synthesis of the naturally occurring pyrrolizidine alkaloid (+)-latifoline (1) employing a tandem [3,3] sigmatropic rearrangement/[1,2] allyl shift as a key step in constructing (+)-latifolic acid (4).
Drutu
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I
Department of Chemistry, Yale University, Sterling Chemistry Laboratory, P.O. Box 208107, New Haven, Connecticut 06520-8107, USA.
Krygowski
E S
ES
Wood
J L
JL
D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D028082:Boraginaceae / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis*; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D007783:Lactones; D011763:Pyrrolizidine Alkaloids; C459704:latifolic acid; C459703:latifoline