Toward the macrocidins: macrocyclization via Williamson etherification of a phenolate.

Bertram Barnickel, Rainer Schobert

Organisch-chemisches Laboratorium der Universität Bayreuth, Gebäude NW I, D-95440 Bayreuth, Germany.

The Journal of organic chemistry 2010 Oct 1

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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.

Citation

Bertram Barnickel, Rainer Schobert. Toward the macrocidins: macrocyclization via Williamson etherification of a phenolate. The Journal of organic chemistry. 2010 Oct 1;75(19):6716-9