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Synthesis of Cycleanine Mono-N-oxides 1998
Research Laboratories, Kaken Shoyaku Co., Ltd., 3-37-10, Shimorenjaku, Mitaka-shi, Tokyo 181, Japan, and Showa College of Pharmaceutical Sciences, 3-3165, Higashi-Tamagawagakuen, Machida-shi, Tokyo 194, Japan.
Oxidation of cycleanine (3) with m-chloroperbenzoic acid gave two diastereomeric N-oxides (1 and 2), and their stereochemistry was unambiguously determined on the basis of spectroscopic evidence. The NMR spectra of synthetic cycleanine mono-N-oxides 1 and 2 were significantly different from those of the natural product previously reported to be cycleanine N-oxide.
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