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Inspired by their potential biosynthesis, we have developed divergent total syntheses of seven monoterpene indole alkaloids including mersicarpine, leuconodines B and D, leuconoxine, melodinine E, leuconolam, and rhazinilam, and one unnatural analogue with an unprecedented structural skeleton. The key steps involve a Witkop-Winterfeldt oxidative indole cleavage followed by transannular cyclization. The transannular cyclization product was then converted to the corresponding structural skeletons by pairing its functional groups into different reaction modes.

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Biosynthetically Inspired Divergent Approach to Monoterpene Indole Alkaloids: Total Synthesis of Mersicarpine, Leuconodines B and D, Leuconoxine, Melodinine E, Leuconolam, and Rhazinilam