Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 12, Issue 22, Pages 3686-3700Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4ob00448e
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Funding
- Croucher Foundation (Hong Kong)
- National Natural Science Foundation of China [NSFC: 21202186, 21272199]
- Shenzhen Science and Technology Innovation Committee [ZDSY20130401150914965]
- Shenzhen Basic Research Program [JCYJ20120619151721025]
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The first enantioselective total synthesis of epiplakinic acid F (1) was achieved through a pivotal step involving a radical-mediated asymmetric peroxidation of vinylcyclopropanes with molecular oxygen to construct highly substituted 1,2-dioxolanes. Subsequent conversions of the chiral 1,2-dioxolanes led to total synthesis of epiplakinic acid F (1) and the confirmation of its absolute configuration. The enantiomer of epiplakinic acid F methyl ester (2) was also prepared.
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