The Revised Structure, Total Synthesis, and Absolute Configuration of Streptophenazine A
Organic Letters2011Vol. 13(20), pp. 5436–5439
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Zhicai Yang, Xiaomin Jin, Michael A. Guaciaro, Bruce F. Molino, Ursula Mocek, Ricardo F. Reátegui, Joshua Rhea, Tim Morley
Abstract
A total synthesis of both diastereomers of the originally proposed structure for streptophenazine A (1) has been achieved. However, both synthetic compounds are different from the natural product. Re-examination of NMR data reported for streptophenazine A and a concise total synthesis of both diastereomers of 17 (17a and 17b) led to the structural revision of streptophenazine A to 17b. Asymmetric synthesis of (-)-streptophenazine A was also conducted, and its absolute configuration was determined to be 1'S,2'R.
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