Biomimetic synthesis of Nauclea indole alkaloids, naucleidinal, and 3-epi-naucleidinal, by stereoselective rearrangement of strictosamide and the vincoside lactam aglycones

Based on a biogenetic consideration, a Nauclea alkaloid, naucleidinal (6), and its 3-epimer (7) were stereoselectively prepared from the aglycones of strictosamide and the vincoside lactam, and their absolute stereochemistry was confirmed.