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Total Synthesis of (-)-Nahuoic Acid Ci (Bii).

ABSTRACT: 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.

SUBMITTER: Liu Q

PROVIDER: S-EPMC5655813 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature

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Total Synthesis of (-)-Nahuoic Acid Ci (Bii).

Liu Qi Q Deng Yifan Y Smith Amos B AB

Journal of the American Chemical Society 20170921 39

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. ...[more]

PMID: 28933833

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