Total synthesis of muricadienin, the putative key precursor in the solamin biosynthesis.
The first total synthesis of muricadienin, the unsaturated putative precursor in the biosynthesis of trans- and cis-solamin is described. Key steps in the synthesis are a chemoselective hydroboration, a Z-selective Wittig reaction, and a Fries rearrangement for introducing the terminal α-substituted butenolide. Thus, muricadienin can be synthesized in 11 steps from commercially available starting materials in 42% overall yield.
Fachbereich Chemie, Institut für Organische Chemie, Universität Hamburg , Martin-Luther-King Platz 6, 20146 Hamburg, Germany.
Juliane
J
Adrian
Christian B W
CB
Stark
D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000737:chemistry; D054378:Acetogenins / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D054378:Acetogenins; D005663:Furans; C519987:cis-solamin; C000599601:muricadienin; C004511:butenolide; D015107:4-Butyrolactone