Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 17, Pages 7945-7951Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b01730
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Funding
- Iowa State University and National Science Foundation [CHE-CAREER 1353819]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1352080] Funding Source: National Science Foundation
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An enantioselective model synthesis of the 2,3-dihydro-1H-pyrrolo[1,2-a]indole core of the putative structure of yuremamine is reported in 39% overall yield and 96% ee over five steps. The model synthesis leverages enantioselective, rhodium catalyzed hydroacylation of an N-vinylindole-2-carboxaldehyde as the key step in the installation of the stereochemical triad. An enantioselective synthesis of a densely functionalized dihydropyrroloindolone that maps onto the putative structure of yuremamine is demonstrated in 26% yield and 97% ee over eight steps.
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