Concepedia

Enantioselective synthesis of the carbocyclic nucleoside (−)-abacavir

Grant A. Boyle, Christopher D. Edlin, Yongfeng Li, Dennis C. Liotta, Garreth L. Morgans, Chitalu C. Musonda

Organic & Biomolecular Chemistry · 2011 · 23 citations · 28 references

DOI

Concepts

Abstract

An enantiopure β-lactam with a suitably disposed electron withdrawing group on nitrogen, participated in a π-allylpalladium mediated reaction with 2,6-dichloropurine tetrabutylammonium salt to afford an advanced cis-1,4-substituted cyclopentenoid with both high regio- and stereoselectivity. This advanced intermediate was successfully manipulated to the total synthesis of (-)-Abacavir.

References

28

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