The chemical reactivity of cryptophycin 52 towards sulfur and phosporous nucleophiles under different conditions was explored to reveal the differential reactivity of the epoxide and olefinic centers. Under basic conditions 1,4-addition to the enone is favored, while under acidic conditions the epoxide is more reactive. © 2002 Published by Elsevier Science Ltd.
Martinelli, M. J., Vaidyanathan, R., Khau, V. V., & Staszak, M. A. (2002). Reaction of cryptophycin 52 with thiols. Tetrahedron Letters, 43(18), 3365–3367. https://doi.org/10.1016/S0040-4039(02)00553-1