Total synthesis of jimenezin via an intramolecular allylboration.
[structure: see text] An efficient total synthesis of the annonaceous acetogenin jimenezin was achieved. The key steps used were a highly stereoselective intramolecular allylboration to establish the tetrahydropyran ring and an intramolecular Williamson reaction to close the tetrahydrofuran ring.
Bandur
Nina G
NG
Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Strasse, 35032 Marburg, Germany.
Brückner
David
D
Hoffmann
Reinhard W
RW
Koert
Ulrich
U
D054378:Acetogenins; D005233:Fatty Alcohols / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000737:chemistry; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D031045:Rollinia / Q000737:chemistry; D013237:Stereoisomerism
D054378:Acetogenins; D005233:Fatty Alcohols; D005663:Furans; D007783:Lactones; D011714:Pyrans; C410435:jimenezin