trans-epoxy quinols (e.g. 3 )  are present in the natural products bromoxone, harveynone, panepoxydon and others.  For our purposes, trans-epoxy quinol 3  was identified as an early intermediate in the asymmetric total synthesis of antascomicin B.  Racemic epoxy quinol has been prepared in four steps from benzoquinone.  However, the existing asymmetric synthesis of the corresponding silyl ether required eight steps, high enzyme loading, and long reaction times.  Our goal was to prepare large quantities of the trans-epoxy quinol 3  with an efficiency comparable to the racemic synthesis.  We will describe the successful realization of this goal using Noyori asymmetric transfer hydrogenation of meso-epoxy diketone (figure 1).  The overall asymmetric route is equal in length and higher in reduction diastereoselectivity than the racemic route.

Synthesis of <i>trans</i>-epoxy quinol via Noyori asymmetric transfer hydrogenation of meso-epoxy diketone

243rd National Meeting (2012)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.

Synthesis of trans-epoxy quinol via Noyori asymmetric transfer hydrogenation of meso-epoxy diketone