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Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
The revised structure, total synthesis, and absolute configuration of streptophenazine A
Zhicai Yang1, Xiaomin Jin, Michael Guaciaro
1Medicinal Chemistry Department, AMRI, 26 Corporate Circle, P.O. Box 15098, Albany, New York 12212-5098, USA. zhicai.yang@amriglobal.com
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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