A diastereoselective oxa-Pictet-Spengler-based strategy for (+)-frenolicin B and epi-(+)-frenolicin B synthesis.

@article{Zhang2013ADO,
  title={A diastereoselective oxa-Pictet-Spengler-based strategy for (+)-frenolicin B and epi-(+)-frenolicin B synthesis.},
  author={Yinan Zhang and Xiachang Wang and Manjula Sunkara and Qing Ye and Larissa V. Ponomereva and Qing-Bai She and Andrew J. Morris and Jon S. Thorson},
  journal={Organic letters},
  year={2013},
  volume={15 21},
  pages={
          5566-9
        }
}
An efficient diastereoselective oxa-Pictet-Spengler reaction strategy was developed to construct benzoisochroman diastereomers. The utility of the reaction was demonstrated in the context of both the total synthesis of naturally occurring pyranonaphthoquinones (+)-frenolicin B and epi-(+)-frenolicin B as well as a range of frenolicin precursor analogs. The method is versatile and offers exquisite stereocontrol and, as such, offers a synthetic advance for the synthesis of pyranonaphthoquinone… 
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