Improved synthesis of (R)-7-hydroxycarvone from (S)-α-pinene

A three-step synthesis of (R)-7-hydroxycarvone (1), which is anticipated to be a valuable building block for the versatile preparation of natural products, is described. Optimization of the reaction conditions for photooxygenation and migration of (S)-alpha-pinene 2, tetrapropylammonium perruthenate (TPAP) oxidation of the generated alcohol, and a subsequent ring-opening reaction in the presence of Cu(OTt)(2) led to the synthesis of 1 with good reproducibility. The desired product 1 was thus obtained in 46% yield over three steps. (C) 2013 Elsevier Ltd. All rights reserved.