Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 135, Issue 34, Pages 12568-12571Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja406657v
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Funding
- Japan Society for the Promotion of Science (JSPS) [25460020, 25860010]
- Quality Assurance Framework of Higher Education from The Ministry of Education, Culture, Sports, Science and Technology (MEXT) [23105012]
- Grants-in-Aid for Scientific Research [25860010, 24790021, 24102527, 24790022, 25460020] Funding Source: KAKEN
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A first asymmetric total synthesis and determination of the absolute configuration of neoxaline has been accomplished through the highly stereoselective introduction of a reverse prenyl group to create a quaternary carbon stereocenter using (-)-3a-hydroxyfuroindoline as a building block, construction of the indoline spiroaminal via cautious stepwise oxidations with cyclizations from the indoline, assembly of (Z)-dehydrohistidine, and photoisomerization of unnatural (Z)-neoxaline to the natural (E)-neoxaline as the key steps.
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