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

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 g...

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Veröffentlicht in:	Organic letters 2016-04, Vol.18 (8), p.1912-1915
Hauptverfasser:	Kitajima, Mariko, Watanabe, Keisuke, Maeda, Hiroyuki, Kogure, Noriyuki, Takayama, Hiromitsu
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkaloids - chemical synthesis Alkaloids - chemistry Catalysis Cyclization Indole Alkaloids - chemical synthesis Indole Alkaloids - chemistry Magnetic Resonance Spectroscopy Molecular Structure Stereoisomerism
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Zusammenfassung:	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.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/acs.orglett.6b00661