Stereocontrolled Synthesis of C-Arylglycosides Applied to the South West Fragment of the Antibiotic Kendomycin

Abstract

A nine step synthesis of the southwest fragment 3 of the antibiotic kendomycin (1) is reported. The tetrahydropyran ring is prepared in a highly stereocontrolled and efficient sequence. The key step concerns an anti-aldol reaction using chiral ketone 10. C-Aryl glycoside 3 exhibits atropisomerism and the relative configuration around its tetrahydropyran ring was established by NOE experiments.

Key words

total synthesis - natural products - aldol reactions - glycosides - atropisomerism - antibiotics

References

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