Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 43, Pages 13764-13767Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b09198
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Funding
- Ministry of Science Technology [2013CB836900]
- National Natural Science Foundation of China [21525209, 21290180, 21172235, 21222202, 21302204]
- Shanghai Science and Technology Commission [15JC1400400]
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The total synthesis of epoxyeujindole A, a structurally unusual indole diterpenoid isolated from Eupenicillium javanicum, has been accomplished for the first time. The synthesis features a late-stage cationic cyclization strategy, which took advantage of an electron-rich olefinic substrate. The CDE ring system was assembled via an enantioselective conjugate addition/alkylation, a Luche cyclization, and a Nozaki-Hiyama-Kishi reaction. The heavily substituted A ring was constructed through a Suzuki-Miyaura coupling and a cationic cyclization, and the bridged fused B ring was formed through a Prins reaction.
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