No protecting groups were required in a concise and atom-economical synthesis of the optically active tetracyclic pyrrolidine 3 under mild conditions. A highly diastereoselective Pauson–Khand reaction (1→2) was used to construct the compact tetracycle with its quaternary stereocenter. The stereoselectivity of the cycloaddition was affected by the substituent on the propargylic moiety.
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Jiang et al. (2004) studied this question.
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