Total synthesis of phoslactomycin A.
A convergent total synthesis of the PP2A-inhibitor phoslactomycin A was achieved using a CuTC-mediated coupling of an alkenyl iodide C1-C13 fragment with an C14-C21 alkenyl stannane in the presence of a protected phosphate. Key features for the assembly of the C1-C13 fragment were an asymmetric dihydroxylation, an Evans-Aldol reaction, and a well-balanced protective group strategy. An asymmetric 1,4-addition to cyclohexenone was the key step in the preparation of the C14-C21 fragment.
König
Christian M
CM
Fachbereich Chemie, Philipps-University Marburg, Hans-Meerwein-Strasse, D-35032 Marburg, Germany.
Gebhardt
Björn
B
Schleth
Cornelia
C
Dauber
Mario
M
Koert
Ulrich
U
D002384:Catalysis; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D054648:Protein Phosphatase 2 / Q000037:antagonists & inhibitors*; D011753:Pyrones; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry
D007783:Lactones; D009943:Organophosphorus Compounds; D011753:Pyrones; C060448:phoslactomycin A; D054648:Protein Phosphatase 2