Tandem radical cyclizations with iodoaryl azides: formal total synthesis of (+/-)-aspidospermidine.
An iodoazide radical cascade cyclization strategy has been used as the key step in a formal synthesis of aspidospermidine. Specifically, this step generated the alkaloid's B- and E-rings in the ethylidene-functionalized tetracycle 5. In turn, this was converted into pentacycle 25, a known advanced synthetic precursor of aspidospermidine.
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Department of Pure and Applied Chemistry, 295 Cathedral Street, Glasgow G1 1XL, U.K.
Murphy
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JA
D000470:Alkaloids / Q000138:chemical synthesis*; D001386:Azides; D003500:Cyclization; D007202:Indicators and Reagents; D026121:Indole Alkaloids; D007211:Indoles; D011804:Quinolines; D013237:Stereoisomerism
D000470:Alkaloids; D001386:Azides; D007202:Indicators and Reagents; D026121:Indole Alkaloids; D007211:Indoles; D011804:Quinolines; C409672:aspidospermidine