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A Formal Total Synthesis of (±)-Kopsihainanine A Using a Raney-Cobalt Mediated Reductive Cyclization Route to Polyhydroquinolines

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journal contribution
posted on 15.07.2016, 00:00 by Shen H. Tan, Martin G. Banwell, Anthony C. Willis
Perhydroquinoline 4, the product of a Raney-cobalt mediated reductive cyclization reaction, was readily converted into the cis-ring-fused perhydroquinoline 15 that could be epimerized to its trans-fused counterpart 2 on sequential treatment with iodosylbenzene then sodium borohydride. Tetracycle 2 is an advanced intermediate associated with a recently reported total synthesis of the alkaloid kopsihainanine A (1).

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