Assignment of the C5′ Relative Stereochemistry in (+)-Lepadin F and (+)-Lepadin G and Absolute Configuration of (+)-Lepadin G

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Abstract

Concise assignments of the C5' stereochemistry in (+)-lepadin F and (+)-lepadin G and the absolute configuration of (+)-lepadin G via the first total syntheses of (+)-5'-epi-lepadin F, (+)-lepadin G, and (+)-5'-epi-lepadin G are described. This work represents an illustrative example in which a diastereomeric pair can possess sufficient spectroscopic difference for clear assignment despite differing only at a highly insulated acyclic stereocenter.

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