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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.

Postulated Biogenesis-Guided Total Synthesis and Structural Revision of 2,18-seco-Lankacidinol A