Abstract
A modular, eight-step synthesis of bengamide E and six analogues from a common chiral pool has been developed. The key step in this approach is a cross-metathesis coupling of various commercial terminal olefins and a common alkene bearing the required stereogenic centers of bengamides lateral chain, which was easily derived from α-d-glucoheptonic-γ-lactone. Complete E-selectivity, and up to 92% yield were achieved for this crucial cross-metathesis step.
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