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

Mariko Kitajima; Keisuke Watanabe; Hiroyuki Maeda; Noriyuki Kogure; Hiromitsu Takayama

doi:10.1021/acs.orglett.6b00661

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. Epub 2016 Apr 1.

Authors

Mariko Kitajima¹, Keisuke Watanabe¹, Hiroyuki Maeda¹, Noriyuki Kogure¹, Hiromitsu Takayama¹

Affiliation

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / chemical synthesis*
Alkaloids / chemistry
Catalysis
Cyclization
Indole Alkaloids / chemical synthesis*
Indole Alkaloids / chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Stereoisomerism

Substances

Alkaloids
Indole Alkaloids
gardnerine
hydroxygardnerine
koumine
macusine B
sarpagine