Asymmetric synthesis of 1-deoxynojirimycin and its congeners from a common chiral building block

Hiroki Takahata; Yasunori Banba; Mayumi Sasatani; Hideo Nemoto; Atsushi Kato; Isao Adachi

doi:10.1016/j.tet.2004.06.112

Asymmetric synthesis of 1-deoxynojirimycin and its congeners from a common chiral building block

Hiroki Takahata, Yasunori Banba, Mayumi Sasatani, Hideo Nemoto, Atsushi Kato, Isao Adachi

Hospital Pharmacy

Research output: Contribution to journal › Article › peer-review

81 Scopus citations

Abstract

A new, promising chiral building block 9 for the synthesis of 1-deoxy-4,5-trans-oriented azasugars such as 1-deoxynojirimycin (1) was prepared in only four steps from the Garner aldehyde 10 using catalytic ring-closing metathesis (RCM) for the construction of the piperidine ring. In practical test, the first synthesis of all four isomers (1 and 6-8) of trans-4,5-orientated 1-deoxyiminosugars using 9 as a common chiral building block was demonstrated. Graphical Abstract

Original language	English
Pages (from-to)	8199-8205
Number of pages	7
Journal	Tetrahedron
Volume	60
Issue number	37
DOIs	https://doi.org/10.1016/j.tet.2004.06.112
State	Published - 2004/09/06

Keywords

Asymmetric synthesis
Garner aldehyde
Iminosugars

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2004.06.112

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title = "Asymmetric synthesis of 1-deoxynojirimycin and its congeners from a common chiral building block",

abstract = "A new, promising chiral building block 9 for the synthesis of 1-deoxy-4,5-trans-oriented azasugars such as 1-deoxynojirimycin (1) was prepared in only four steps from the Garner aldehyde 10 using catalytic ring-closing metathesis (RCM) for the construction of the piperidine ring. In practical test, the first synthesis of all four isomers (1 and 6-8) of trans-4,5-orientated 1-deoxyiminosugars using 9 as a common chiral building block was demonstrated. Graphical Abstract",

keywords = "Asymmetric synthesis, Garner aldehyde, Iminosugars",

author = "Hiroki Takahata and Yasunori Banba and Mayumi Sasatani and Hideo Nemoto and Atsushi Kato and Isao Adachi",

note = "Funding Information: This research was supported by the Uehara Memorial Foundation and a Grant-in-Aid for Scientific Research on Priority Areas (A) {\textquoteleft}Exploitation of Multi-Element Cyclic Molecules{\textquoteright} from the Ministry of Education, Culture, Sports, Science and Technology, Japan.",

year = "2004",

month = sep,

day = "6",

doi = "10.1016/j.tet.2004.06.112",

language = "英語",

volume = "60",

pages = "8199--8205",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd.",

number = "37",

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TY - JOUR

T1 - Asymmetric synthesis of 1-deoxynojirimycin and its congeners from a common chiral building block

AU - Takahata, Hiroki

AU - Banba, Yasunori

AU - Sasatani, Mayumi

AU - Nemoto, Hideo

AU - Kato, Atsushi

AU - Adachi, Isao

N1 - Funding Information: This research was supported by the Uehara Memorial Foundation and a Grant-in-Aid for Scientific Research on Priority Areas (A) ‘Exploitation of Multi-Element Cyclic Molecules’ from the Ministry of Education, Culture, Sports, Science and Technology, Japan.

PY - 2004/9/6

Y1 - 2004/9/6

N2 - A new, promising chiral building block 9 for the synthesis of 1-deoxy-4,5-trans-oriented azasugars such as 1-deoxynojirimycin (1) was prepared in only four steps from the Garner aldehyde 10 using catalytic ring-closing metathesis (RCM) for the construction of the piperidine ring. In practical test, the first synthesis of all four isomers (1 and 6-8) of trans-4,5-orientated 1-deoxyiminosugars using 9 as a common chiral building block was demonstrated. Graphical Abstract

AB - A new, promising chiral building block 9 for the synthesis of 1-deoxy-4,5-trans-oriented azasugars such as 1-deoxynojirimycin (1) was prepared in only four steps from the Garner aldehyde 10 using catalytic ring-closing metathesis (RCM) for the construction of the piperidine ring. In practical test, the first synthesis of all four isomers (1 and 6-8) of trans-4,5-orientated 1-deoxyiminosugars using 9 as a common chiral building block was demonstrated. Graphical Abstract

KW - Asymmetric synthesis

KW - Garner aldehyde

KW - Iminosugars

UR - http://www.scopus.com/inward/record.url?scp=4143147593&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2004.06.112

DO - 10.1016/j.tet.2004.06.112

M3 - 学術論文

AN - SCOPUS:4143147593

SN - 0040-4020

VL - 60

SP - 8199

EP - 8205

JO - Tetrahedron

JF - Tetrahedron

IS - 37

ER -

Asymmetric synthesis of 1-deoxynojirimycin and its congeners from a common chiral building block

Abstract

Keywords

ASJC Scopus subject areas

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