期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 137, 期 32, 页码 10160-10163出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b07154
关键词
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资金
- NIH/NIGMS [GM-073949]
- NSF
- DAAD
- JSPS
- Grants-in-Aid for Scientific Research [14J03546] Funding Source: KAKEN
Verruculogen and fumitremorgin A are bioactive alkaloids that contain a unique eight-membered endoperoxide. Although related natural products such as fumitremorgins B and C have been previously synthesized, we report the first synthesis of the more complex, endoperoxide-containing members of this family. A concise route to verruculogen and fumitremorgin A relied not only on a hydroperoxide/indole hemiaminal cyclization, but also on the ability to access the seemingly simple starting material, 6-methoxytryptophan. An iridium-catalyzed C-H borylation/Chan-Lam procedure guided by an N-TIPS group enabled the conversion of a tryptophan derivative into a 6-methoxytryptophan derivative, proving to be a general way to functionalize the C6 position of an N,C3-disubstituted indole for the synthesis of indole-containing natural products and pharmaceuticals.
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