2. Academic Validation
  3. Total Synthesis of Viridin and Viridiol

Total Synthesis of Viridin and Viridiol

  • J Am Chem Soc. 2019 Oct 16;141(41):16208-16212. doi: 10.1021/jacs.9b08577.
Yang Ji 1,  Zhengyuan Xin 1,  Haibing He 2,  Shuanhu Gao 1 2
Affiliations

Affiliations

  • 1 Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering , East China Normal University , 3663N Zhongshan Road , Shanghai 200062 , China.
  • 2 Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development , East China Normal University , 3663N Zhongshan Road , Shanghai 200062 , China.
PMID: 31554399 DOI: 10.1021/jacs.9b08577
Abstract

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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