Total Syntheses of 3- epi-Litsenolide D 2 and Lincomolide A

The first total syntheses of 3- epi-litsenolide D and its enantiomer lincomolide A were achieved. The synthetic highlights of our approach include olefin cross metathesis and bromine addition to the generated double bond, followed by the regioselective HBr-elimination and intramolecular carbonylatio...

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Bibliographic Details
Published in:Journal of organic chemistry 2018-09, Vol.83 (18), p.11450-11457
Main Authors: Kutsumura, Noriki, Kiriseko, Akito, Niwa, Kentaro, Saito, Takao
Format: Article
Language:English
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Summary:The first total syntheses of 3- epi-litsenolide D and its enantiomer lincomolide A were achieved. The synthetic highlights of our approach include olefin cross metathesis and bromine addition to the generated double bond, followed by the regioselective HBr-elimination and intramolecular carbonylation using bis(triphenylphosphine)dicarbonylnickel. This investigation also revealed that the previously reported specific optical rotation of 3- epi-litsenolide D should be revised.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b01825