Tronocarpine (1) and dippinine B (2) are structurally unique indole alkaloids that were isolated from the stem extract of the Malaysian plant Tabernaemontana corymbosa in 2000 and 2001, respectively. Dippinine B (2), containing a pentacyclic framework, was found to reverse multidrug resistance in vincristine-resistant KB cells. The bioactivity of tronocarpine (1), containing a novel pentacyclic skeleton incorporating a seven-membered lactam, has not been determined due to its low natural abundance. Progress towards the first total syntheses of these metabolites from a common late stage intermediate 3 will be discussed.

Studies on total syntheses of tronocarpine and dippinine B

2019 Spring National Meeting

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