Journal
ORGANIC LETTERS
Volume 15, Issue 21, Pages 5566-5569Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol4027649
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Funding
- University of Kentucky College of Pharmacy
- University of Kentucky Markey Cancer Center
- National Institutes of Health [CA175105]
- National Center for Advancing Translational Sciences [UL1TR000117]
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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 analogs.
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