Synthetic Studies on Amphirionin-5: Stereochemical Assignment/Reassignment of the C1-C9 Portion through Stereodivergent Synthesis

Synthesis of four diastereomers of the C1-C12 fragment of amphirionin-5 has been achieved in a convergent and stereodivergent manner. Detailed comparison of the H-1 and C-13 NMR data of each compound with those reported for the natural product led to not only the stereochemical assignment of the relative configuration of the C4/C5 stereogenic centers but also reassignment of the proposed relative configuration at C9 of amphirionin-5.