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Published on: January 13, 2017
Postulated Biogenesis-Guided Total Synthesis and Structural Revision of 2,18-seco-Lankacidinol A
Kuan Zheng1,2, Ran Hong1
1CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
Abstract:
The macrocyclic structure of 2,18-seco-lankacidinol A, a newly isolated antitumor antibiotic, has been revised on the basis of a concise modular synthesis inspired by a reconsidered biosynthetic proposal. Notable features include (1) an acid-promoted intramolecular transacetalization of a N-lactoyl-O-methyl-N,O-acetal to construct the 4-oxazolidinone ring and (2) late-stage β-keto imide aldolizations that give rise to facile, stereodivergent access to all lactonic diastereomers.
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