Abstract
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.
Original language | English |
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Pages (from-to) | 12568-12571 |
Number of pages | 4 |
Journal | Journal of the American Chemical Society |
Volume | 135 |
Issue number | 34 |
DOIs | |
Publication status | Published - 2013 Aug 28 |
Externally published | Yes |
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
- Biochemistry
- Colloid and Surface Chemistry