Highly stereoselective radical cyclization and olefin metathesis reactions for the construction of oxacyclic building blocks were key steps in the convergent total synthesis of the orally active antifungal agent ambruticin (1).
Radical cyclization of the β-alkoxymethacrylate obtained from 5-benzyloxy-1-iodohexan-3-ol led to the stereoselective preparation of the benzyl
ether of (+)-methyl nonactate, demonstrating “2,5-cis” selectivity in the radical cyclization step in forming a tetrahydrofuran ring system and
“threo” selectivity in the hydrogen abstraction step.
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