Alstoscholarisines B (1) and C (2) are monoterpenoid indole alkaloids that were isolated from the leaves of Alstonia scholaris in 2014 (Figure 1). These metabolites, which contain a unique pentacyclic framework with five contiguous stereocenters, were found to be potent promoters of adult stem cell proliferation and might find use in treatment of neurogenic ailments such as Alzheimer’s, Parkinson’s, or Huntington’s diseases. We have completed the first total syntheses of these molecules starting from indole ester 3 and α,β-unsaturated lactam 4.

Divergent total syntheses of (±)-alstoscholarisines B and C

255th National Meeting (2018)

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