Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 30, Pages 10384-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja9039407
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- National Institute of Health [GM-61591]
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The first total synthesis of (-)-plicatic acid has been achieved by a concise and enantiosetective route. In this synthesis, a conceptually new strategy featuring an A asymmetric epoxidation-intramolecular epoxy-ring-opening Friedel-Crafts reaction sequence was developed for the stereoselective construction of the 2,7'-cyclolignane skeleton bearing contiguous quaternary-quaternary-tertiary stereocenters. The implementation of this strategy was enabled by the development of a modified protocol for the Seebach epoxiclation with TADOOH, which affords an unprecedented, highly enantiosetective and diastereoselective epoxiclation with a range of alpha-carbonyl-B-substituted acrylates 3.
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