212. Total Synthesis of the Lycorenine-Type Amaryllidaceae Alkaloid (±)-Clivonine via a Biomimetic Ring-Switch from a Lycorine-Type Progenitor
     Mañas, C. G.; Paddock, V. L.; Bochet, C. G.; Spivey, A. C.; White, A. J. P.; Mann, I.; Oppolzer, W.
     J. Am. Chem. Soc. 2010, 132, 5176-5178

A fully diastereoselective total synthesis of the lycorenine-type Amaryllidaceae alkaloid (±)-clivonine (19) is reported via a route that employs for the first time a biomimetic ring-switch from a lycorine-type progenitor, thereby corroborating experimentally the biogenetic hypothesis first expounded for these compounds by Barton in 1960.

DOI : 10.1021/ja910184j 

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