Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 41, Pages 16208-16212Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b08577
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Funding
- National Basic Research Program of China (973 Program) [2015CB856600]
- National Natural Science Foundation of China [21971068, 21772044]
- National Young Top -Notch Talent Support Program
- Program of Shanghai Academic/Technology Research Leader [18XD1401500]
- Program of Shanghai Science and Technology Committee [18JC1411303]
- Program for Changjiang Scholars and Innovative Research Team in University
- Fundamental Research Funds for the Central Universities
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The asymmetric total synthesis of (-)-viridin and (-)-viridiol, antifungal metabolites, was achieved in 17 and 18 steps from a commercially available starting material. An intramolecular [3+2] cycloaddition was applied to an easily available L-ribose derivative in order to construct the highly substituted D ring containing the key chiral cis-triol fragment. Co-catalyzed metal-hydride H atom transfer (MHAT) radical cyclization was utilized to form the C-ring and the all-carbon quaternary center at C-10. This convergent strategy provides a scalable approach to prepare viridin and viridiol for biological studies.
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