Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 18, Pages 12187-12191Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01846
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Funding
- William K. Warren Family and Foundation
- Chair in Medicine
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A concise formal total synthesis of pericoannosin A, by the synthesis of an advanced intermediate of pericoannosin A, was achieved in eight steps from commercially available isoprene in a 21.7% overall yield. Key transformations for this expedited route include an enantio- selective organocatalytic Diels-Alder reaction to construct the C ring, a diastereoselective reduction (under Felkin-Ahn control), and a hydroboration/oxidation sequence for chain homologation. This work represents the second synthetic effort toward pericoannosin A, the only reported natural product based on a hexahydro-1H-isochromen-5-isobutylpyrrolidin-2-one core.
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