Synthesis of Cycleanine Mono-N-oxides

N Kashiwaba; M Ono; J Toda; H Suzuki; T Sano

doi:10.1021/np970362t

Synthesis of Cycleanine Mono-N-oxides

J Nat Prod. 1998 Feb 27;61(2):253-5. doi: 10.1021/np970362t.

Authors

N Kashiwaba¹, M Ono, J Toda, H Suzuki, T Sano

Affiliation

¹ 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.

PMID: 9548855
DOI: 10.1021/np970362t

Abstract

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.