Toward the macrocidins: macrocyclization via Williamson etherification of a phenolate.
The synthesis of macrocyclic 3-acyltetramic acids which are immediate precursors of the fungal herbicide macrocidin A (1) is reported. The crucial closure of the macrocycle was achieved in excellent yield by an unprecedented Williamson etherification of an ω-bromo phenolate generated in situ by a Pd-mediated O-deallylation.
Barnickel
Bertram
B
Organisch-chemisches Laboratorium der Universität Bayreuth, Gebäude NW I, D-95440 Bayreuth, Germany.
Schobert
Rainer
R
D003500:Cyclization; D047028:Macrocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry*; D011760:Pyrrolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D000097566:Cyclophanes
D047028:Macrocyclic Compounds; D010636:Phenols; D011760:Pyrrolidinones; C482758:macrocidin A; D000097566:Cyclophanes