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Journal Article
Research Support, N.I.H., Extramural
Total Synthesis of (-)-Nahuoic Acid C i (B ii ).
Journal of the American Chemical Society 2017 October 5
A convergent total synthesis of (-)-nahuoic acid Ci (Bii ) (3), a novel cis-decalin polyketide, has been achieved. Key synthetic transformations include Type II Anion Relay Chemistry (ARC) to construct the polyol chain, a Ti-catalyzed asymmetric Diels-Alder reaction to generate the cis-decalin skeleton, and a late-stage large fragment union exploiting a Micalizio alkoxide-directed alkyne-alkene coupling tactic.
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