摘要

Pyrano-naphthoquinones fused to gamma-lactone ring are structurally and biologically interesting natural products. We have accomplished an enantioselective synthesis of (-)-arizonin C1 (2d) in nine steps. We employed the Sharpless dihydroxylation of beta,gamma-unsaturatedester 9d as a highly enantioselec-tive (>99% ee) access to the.-lactone intermediate 7d. Oxa-Pictet-Spengler cyclization, oxidation, and epimerization as expected led to the conversion of 7d into 2d. The pentasubstituted naphthalene precursor 14 of ester 9d was obtained by Dotz benzannulation.

  • 出版日期2011-9