Abstract
The stereoselective total synthesis of (+)-galanthamine (+)-1 starting from d-glucose is described. The cyclohexene ring in (+)-1 was prepared in an optically active form from d-glucose using Ferrier's carbocyclization reaction, and the critical quaternary carbon was stereoselectively generated via chirality transfer based on the Claisen rearrangement of a cyclohexenol. The dibenzofuran skeleton was effectively constructed by the bromonium ion-mediated intramolecular cyclization of a cyclohexene possessing a phenolic ether function. After the introduction of a carbon-carbon double bond, the Pictet-Spengler type cyclization, followed by the reduction of the amide function completed the chiral synthesis of (+)-1.
| Original language | English |
|---|---|
| Pages (from-to) | 6267-6270 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 48 |
| Issue number | 36 |
| DOIs | |
| Publication status | Published - 2007 Sep 3 |
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Keywords
- Chiral synthesis
- Claisen rearrangement
- Galanthamine
ASJC Scopus subject areas
- Biochemistry
- Organic Chemistry
- Drug Discovery
Cite this
Total synthesis of (+)-galanthamine starting from d-glucose. / Tanimoto, Hiroki; Kato, Tomoaki; Chida, Noritaka.
In: Tetrahedron Letters, Vol. 48, No. 36, 03.09.2007, p. 6267-6270.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Total synthesis of (+)-galanthamine starting from d-glucose
AU - Tanimoto, Hiroki
AU - Kato, Tomoaki
AU - Chida, Noritaka
PY - 2007/9/3
Y1 - 2007/9/3
N2 - The stereoselective total synthesis of (+)-galanthamine (+)-1 starting from d-glucose is described. The cyclohexene ring in (+)-1 was prepared in an optically active form from d-glucose using Ferrier's carbocyclization reaction, and the critical quaternary carbon was stereoselectively generated via chirality transfer based on the Claisen rearrangement of a cyclohexenol. The dibenzofuran skeleton was effectively constructed by the bromonium ion-mediated intramolecular cyclization of a cyclohexene possessing a phenolic ether function. After the introduction of a carbon-carbon double bond, the Pictet-Spengler type cyclization, followed by the reduction of the amide function completed the chiral synthesis of (+)-1.
AB - The stereoselective total synthesis of (+)-galanthamine (+)-1 starting from d-glucose is described. The cyclohexene ring in (+)-1 was prepared in an optically active form from d-glucose using Ferrier's carbocyclization reaction, and the critical quaternary carbon was stereoselectively generated via chirality transfer based on the Claisen rearrangement of a cyclohexenol. The dibenzofuran skeleton was effectively constructed by the bromonium ion-mediated intramolecular cyclization of a cyclohexene possessing a phenolic ether function. After the introduction of a carbon-carbon double bond, the Pictet-Spengler type cyclization, followed by the reduction of the amide function completed the chiral synthesis of (+)-1.
KW - Chiral synthesis
KW - Claisen rearrangement
KW - Galanthamine
UR - http://www.scopus.com/inward/record.url?scp=34547700961&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=34547700961&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2007.07.042
DO - 10.1016/j.tetlet.2007.07.042
M3 - Article
AN - SCOPUS:34547700961
VL - 48
SP - 6267
EP - 6270
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 36
ER -