Total synthesis of parvaquone and the serendipitous discovery of a novel chromium-mediated method for β-lactone formation

JPA Harrity, WJ Kerr, D Middlemiss, JS Scott

Index: Harrity, Joseph P. A.; Kerr, William J.; Middlemiss, David; Scott, James S. Journal of Organometallic Chemistry, 1997 , vol. 532, # 1-2 p. 219 - 227

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Citation Number: 27

Abstract

During attempts to synthesise the 2-hydroxy-1, 4-naphthoquinone, parvaquone, 1, a novel chromium-mediated method for the synthesis of functionalised β-lactones from propargyl alcohols has been discovered. Additionally, using both dry state and ultrasound conditions, the total synthesis of parvaquone (1) has been achieved: the most efficient techniques deliver this target compound in up to 46% overall yield over, as low as, two synthetic ...