Remote Quaternary Stereocenter Construction toward Crinine-Type Alkaloids Via Chiral Organoiodine-Mediated Biomimetic Oxidative para -Dearomative C–C Coupling

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Abstract Remote stereocontrol in iodine(III)-mediated oxidative phenol dearomatization is challenging because the C–C bond-forming site is distant from the chiral iodine environment. We designed ortho-brominated phenol substrates and a C2-symmetric organoiodine catalyst to enable biomimetic para-dearomative coupling. This strategy constructs remote all-carbon quaternary stereocenters through seven-membered-ring-forming oxidative C–C coupling, enabling total syntheses of (+)-oxomaritidine and (+)-oxovittatine and formal syntheses of (+)-maritidine and (+)-vittatine. The ortho-substituent effects on enantioselectivity suggest that substrate organization may contribute to remote asymmetric induction.

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