In the Weinreb synthesis of Bactobolin A, the CHCl2 moiety was diastereoselectively introduced via addition of Cl2CHLi in the presence of CeCl3 at -100 °C. We hypothesized that finding alternate conditions for introduction of the CHCl2 group may contribute to the future scalability and reproducibility of our synthesis. To this end, we tested conditions developed by Mioskowski for the addition of CCl3 -into ketones. To our surprise, rather than forming 13, these conditions led to inversion of the C4 stereocenter; we note that this stereochemistry matches that found in natural Bactobolin A. A crystal structure of 14 allowed us to confirm product identity and stereochemistry unambiguously (Figure ). Furthermore, we were then able to assign the stereochemistry of 11 by analogy (see Supporting Information for further details).