With the complete skeleton of the dragocin natural product family in hand, bearing a synthetic handle at C-4', a classic Barton decarboxylative chlorination 14 was pursued. Oxidation of the free primary alcohol in 15 to the carboxylic acid was achieved using TPAP•NMO (69% yield). Conveniently, simple exposure of this acid to HOTT 15 in CCl4 at 80 °C led smoothly to the elusive tertiary chloride 16 (48% isolated yield). In general, Barton decarboxylative chlorinations involve the use of acid chlorides or coupling reagents such as DCC, all of which were unsuccessful in our hands, likely due to the sterically encumbered environment. The use of HOTT in CCl4 followed by simple heating, although a seemingly incremental modification, proved essential in this case. To complete the synthesis of dragocin B (1B) and C (1C), global reduction using LAH was successful in delivering the natural products (1B: observed [𝑎] ! "# -16.7°; lit.