Abstract
The stereoselective total synthesis of (+)-galanthamine [(+)-1], an antipode of the natural product, and (-)-galanthamine [(-)-1] starting from D-glucose is described. The cyclohexene unit in (+)-1 was prepared in an optically active form from D-glucose using Ferrier's carbocyclization reaction, and the benzylic quaternary carbon was stereoselectively generated via chirality transfer by Johnson-or Eschenmoser-Claisen rearrangement. The dibenzofuran skeleton was effectively constructed by the bromonium ion-mediated intramolecular dealkylating etherification. After the introduction of a carbon-carbon double bond, the Pictet-Spengler type cyclization, followed by reduction of an amide function afforded (+)-1. Starting from D-glucose, (-)-galanthamine [(-)-1] was also totally synthesized.
| Original language | English |
|---|---|
| Pages (from-to) | 563-597 |
| Number of pages | 35 |
| Journal | Heterocycles |
| Volume | 82 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - 2010 |
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ASJC Scopus subject areas
- Analytical Chemistry
- Organic Chemistry
- Pharmacology
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Total synthesis of (+)- and (-)-galanthamine. / Kato, Tomoaki; Tanimoto, Hiroki; Yamada, Hisako; Chida, Noritaka.
In: Heterocycles, Vol. 82, No. 1, 2010, p. 563-597.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Total synthesis of (+)- and (-)-galanthamine
AU - Kato, Tomoaki
AU - Tanimoto, Hiroki
AU - Yamada, Hisako
AU - Chida, Noritaka
PY - 2010
Y1 - 2010
N2 - The stereoselective total synthesis of (+)-galanthamine [(+)-1], an antipode of the natural product, and (-)-galanthamine [(-)-1] starting from D-glucose is described. The cyclohexene unit in (+)-1 was prepared in an optically active form from D-glucose using Ferrier's carbocyclization reaction, and the benzylic quaternary carbon was stereoselectively generated via chirality transfer by Johnson-or Eschenmoser-Claisen rearrangement. The dibenzofuran skeleton was effectively constructed by the bromonium ion-mediated intramolecular dealkylating etherification. After the introduction of a carbon-carbon double bond, the Pictet-Spengler type cyclization, followed by reduction of an amide function afforded (+)-1. Starting from D-glucose, (-)-galanthamine [(-)-1] was also totally synthesized.
AB - The stereoselective total synthesis of (+)-galanthamine [(+)-1], an antipode of the natural product, and (-)-galanthamine [(-)-1] starting from D-glucose is described. The cyclohexene unit in (+)-1 was prepared in an optically active form from D-glucose using Ferrier's carbocyclization reaction, and the benzylic quaternary carbon was stereoselectively generated via chirality transfer by Johnson-or Eschenmoser-Claisen rearrangement. The dibenzofuran skeleton was effectively constructed by the bromonium ion-mediated intramolecular dealkylating etherification. After the introduction of a carbon-carbon double bond, the Pictet-Spengler type cyclization, followed by reduction of an amide function afforded (+)-1. Starting from D-glucose, (-)-galanthamine [(-)-1] was also totally synthesized.
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UR - http://www.scopus.com/inward/citedby.url?scp=79952256568&partnerID=8YFLogxK
U2 - 10.3987/COM-10-S(E)27
DO - 10.3987/COM-10-S(E)27
M3 - Article
AN - SCOPUS:79952256568
VL - 82
SP - 563
EP - 597
JO - Heterocycles
JF - Heterocycles
SN - 0385-5414
IS - 1
ER -