Synthetic Studies on Amphirionin-5: Stereochemical
Assignment/Reassignment of the C1–C9 Portion through Stereodivergent
Synthesis
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Abstract
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 <sup>1</sup>H and <sup>13</sup>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
