2 research outputs found
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 <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
Stereodivergent Synthesis and Configurational Assignment of the C1–C15 Segment of Amphirionin‑5
The relative configuration
of the C3–C12 portion of amphirionin-5,
a novel marine polyketide with potent cell proliferation-promoting
activity, was established by the stereodivergent synthesis of six
diastereomeric model compounds and comparison of their NMR spectroscopic
data with those reported for the natural product. This study led to
the elucidation of the relative configuration between C4/C5 and C9/C12
and to the reassignment of the proposed configuration of the C9 position
of amphirionin-5