Total synthesis of (±)-cylindrospermopsin

C Xie, MTC Runnegar, BB Snider

Index: Xie, Chaoyu; Runnegar, Maria T. C.; Snider, Barry B. Journal of the American Chemical Society, 2000 , vol. 122, # 21 p. 5017 - 5024

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Citation Number: 46

Abstract

The first total synthesis of the novel hepatotoxin (±)-cylindrospermopson (1) has been accomplished in 20 steps from 4-methoxy-3-methylpyridine (12) in 3.5% overall yield. The substituted piperidine A ring 19 was generated stereospecifically by a four-step sequence using the addition of trimethylsilylethynylmagnesium bromide to 12 to give 16 and stereospecific addition of vinylcuprate to 16 to form 17. The reaction of diamine 26 with ...