The total synthesis of racemic tubotaiwine 8 has been achieved from the tetracyclic intermediate 1, the key steps being the construction of the C(7)-quaternary centre by cyclization of a thionium ion upon the indole 3-position and the introduction of the C(16)-methoxycarbonyl substituent by photochemical rearrangement of the N-methoxycarbonylenamine 7.
J. Gràcia, J. Bonjoch, N. Casamitjana, M. Amat and J. Bosch, J. Chem. Soc., Chem. Commun., 1991, 614 DOI: 10.1039/C39910000614
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