Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 39, Pages 13668-13671Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b08683
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Funding
- NIH [CA-19033, GM-29028]
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A convergent total synthesis of (-)-nahuoic acid C-i(B-ii) (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 DielsAlder reaction to generate the cis-decalin skeleton, and a late-stage large fragment union exploiting a Micalizio alkoxide-directed alkynealkene coupling tactic.
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