The Relative and Absolute Configuration of PF1140

Yuta Fujita, Hiroki Oguri, Hideaki Oikawa

Received: April 1, 2005 / Accepted June 3, 2005
© Japan Antibiotics Research Association

Abstract A potentially general approach for elucidating the absolute configuration of N-hydroxypyridone antibiotics has been developed. One member of this family of antibiotics, PF1140, was efficiently purified from a crude fungal extract following allylation of its N-hydroxyl group. Removal of the resultant allyl group permitted regeneration of the N-hydroxyl group as well as conversion into the corresponding pyridone derivative. The stereochemistry of PF1140 including the absolute configuration was established by X-ray crystallographic analysis of the S-2-methoxy-2-(1-naphthyl)propionic ester derivative.

Keywords antibiotics, PF1140, absolute configuration, N-hydroxypyridone

Hideaki Oikawa (Corresponding author), Y. Fujita, H. Oguri: Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan, E-mail: