Journal
ORGANIC LETTERS
Volume 22, Issue 11, Pages 4176-4179Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c01253
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Funding
- NIH [R35 GM128570., P30 CA023168]
- NSF through the Major Research Instrumentation Program [CHE 1625543]
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An approach toward the 6-7-5 tricyclic carbon skeleton of the hamigeran natural products was developed. The key steps include a benzyne-beta-ketoester annulative ring expansion to form the 7-membered ring, a Nazarov reaction to form the 5-membered ring, a Ni-catalyzed conjugate methyl addition or a Corey-Chaykovsky reaction to install the all-carbon quaternary center, and a Suzuki cross coupling followed by reduction to introduce the isopropyl group.
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