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Relevant academic research and scientific papers

Determination of the absolute structure of (+)-akaterpin

We describe the total synthesis and structural determination of (+)-akaterpin (1), an inhibitor of phosphatidylinositol- specific phospholipase C (PI-PLC). The key features of the synthetic strategy include the resolution of β,γ-unsaturated ketone (±)-2a with chiral sulfoximine 6. The absolute stereochemistry was determined by comparison of the specific optical rotation data of (+)-1 and (-)-1 with that of natural akaterpin.

Synthesis of a potential key intermediate of akaterpin, specific inhibitor of PI-PLC

In order to establish the stereochemistry of akaterpin, a specific inhibitor of PI-PLC, cis-decalin 2 and trans-decalin 3 were prepared. Comparison of NMR spectra of 2 and 3 with those of akaterpin indicated that the upper decalin has a cis-fused structure. Based on the methodology developed here, synthesis of a potential intermediate 32 for the total synthesis of akaterpin was successfully achieved. Further, resolution of β,γ-unsaturated ketone 6 was accomplished using chiral sulfoxyimine. (C) 2000 Elsevier Science Ltd.