Stereo Selective Total Synthesis of 4‐(S)‐Hydroxy‐5‐(R)‐octyldihydrofuran‐2‐one: Harvestmen Lactone.

A facile and stereoselective synthesis of Harvestmen lactone 1 was accomplished in a linear synthetic approach over 14 steps with an overall yield of 10.1 %. This total synthesis was carried out using a chiral pool approach from commercially available D‐glucose. The key reactions employed in this synthetic approach were Wittig reaction, Barton‐McCombie Deoxygenation and 2,2,6,6‐Tetramethylpiperidin‐1‐yl)oxyl (TEMPO) mediated radical oxidation. [ABSTRACT FROM AUTHOR]