Abstract

The first total synthesis of the liana alkaloid ancistrocladisine ( 1a) and of its novel atropisomer 1b is reported. The required mixed aryl coupling is brought about, regiospecifically, by prefixation of the two molecular moieties by an ester-type auxiliary bridge. A methodology is described for the recycling of the undesired, configurationally stable atropisomer 9b, via the “axially prostereogenic” lactone 8 - chiral economy with respect to rotational isomerism.

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