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 (1)H and (13)C 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.