Total synthesis of (+)-galanthamine starting from d-glucose

Hiroki Tanimoto, Tomoaki Kato, Noritaka Chida

Research output: Contribution to journalArticle

50 Citations (Scopus)

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 languageEnglish
Pages (from-to)6267-6270
Number of pages4
JournalTetrahedron Letters
Volume48
Issue number36
DOIs
Publication statusPublished - 2007 Sep 3

Fingerprint

Galantamine
Carbon
Cyclization
Glucose
Chirality
Skeleton
Amides
Ether
Ions
cyclohexene

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 journalArticle

Tanimoto, Hiroki ; Kato, Tomoaki ; Chida, Noritaka. / Total synthesis of (+)-galanthamine starting from d-glucose. In: Tetrahedron Letters. 2007 ; Vol. 48, No. 36. pp. 6267-6270.
@article{104972bfd84c4a7da80f246dcd82934d,
title = "Total synthesis of (+)-galanthamine starting from d-glucose",
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.",
keywords = "Chiral synthesis, Claisen rearrangement, Galanthamine",
author = "Hiroki Tanimoto and Tomoaki Kato and Noritaka Chida",
year = "2007",
month = "9",
day = "3",
doi = "10.1016/j.tetlet.2007.07.042",
language = "English",
volume = "48",
pages = "6267--6270",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "36",

}

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 -