Asymmetric Total Synthesis of Sarpagine-Related Indole Alkaloids Hydroxygardnerine, Hydroxygardnutine, Gardnerine, (E)-16-epi-Normacusine B, and Koumine

  • Org Lett. 2016 Apr 15;18(8):1912-5. doi: 10.1021/acs.orglett.6b00661.
Mariko Kitajima  1 ,  Keisuke Watanabe  1 ,  Hiroyuki Maeda  1 ,  Noriyuki Kogure  1 ,  Hiromitsu Takayama  1
Affiliations
  • 1. Graduate School of Pharmaceutical Sciences, Chiba University , 1-8-1 Inohana, Chuo-ku, Chiba 260-8675, Japan.
PMID: 27035053 DOI: 10.1021/acs.orglett.6b00661
Abstract

Sarpagine-related Indole Alkaloids (-)-hydroxygardnerine, (+)-hydroxygardnutine, (-)-gardnerine, (+)-(E)-16-epi-normacusine B, and (-)-koumine were divergently synthesized via a common intermediate possessing a piperidine ring with an exocyclic (E)-ethylidene side chain, which was constructed by a gold(I)-catalyzed 6-exo-dig cyclization strategy.

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