Total synthesis of d-fagomine and 6-deoxyfagomine

Im Sook Min; Seung In Kim; Seungmin Hong; In Su Kim; Young Hoon Jung

doi:10.1016/j.tet.2013.03.046

Total synthesis of d-fagomine and 6-deoxyfagomine

Im Sook Min, Seung In Kim, Seungmin Hong, In Su Kim, Young Hoon Jung

Department of Pharmacy

Sungkyunkwan University

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

14 Scopus citations

Abstract

Total synthesis of d-fagomine and 6-deoxyfagomine from readily available d-lyxose is described. The key steps included regioselective and diastereoselective amination, hydroboration-oxidation, and Appel reaction. The reaction of 3,4-anti-tribenzyl ether with chlorosulfonyl isocyanate in toluene at 0 °C afforded 3,4-anti-amino alcohol, an essential compound for the preparation of d-fagomine and 6-deoxyfagomine, with a high diastereoselectivity (dr=26:1) in 74% yield. The origin of diastereoselectivity can be explained by the neighboring group effect, which leads to retention of the stereochemistry.

Original language	English
Pages (from-to)	3901-3906
Number of pages	6
Journal	Tetrahedron
Volume	69
Issue number	19
DOIs	https://doi.org/10.1016/j.tet.2013.03.046
State	Published - 13 May 2013

Keywords

Amination
Chlorosulfonyl isocyanate
Deoxyfagomine
Fagomine
Total synthesis

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10.1016/j.tet.2013.03.046

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title = "Total synthesis of d-fagomine and 6-deoxyfagomine",

abstract = "Total synthesis of d-fagomine and 6-deoxyfagomine from readily available d-lyxose is described. The key steps included regioselective and diastereoselective amination, hydroboration-oxidation, and Appel reaction. The reaction of 3,4-anti-tribenzyl ether with chlorosulfonyl isocyanate in toluene at 0 °C afforded 3,4-anti-amino alcohol, an essential compound for the preparation of d-fagomine and 6-deoxyfagomine, with a high diastereoselectivity (dr=26:1) in 74\% yield. The origin of diastereoselectivity can be explained by the neighboring group effect, which leads to retention of the stereochemistry.",

keywords = "Amination, Chlorosulfonyl isocyanate, Deoxyfagomine, Fagomine, Total synthesis",

author = "Min, \{Im Sook\} and Kim, \{Seung In\} and Seungmin Hong and Kim, \{In Su\} and Jung, \{Young Hoon\}",

year = "2013",

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day = "13",

doi = "10.1016/j.tet.2013.03.046",

language = "English",

volume = "69",

pages = "3901--3906",

journal = "Tetrahedron",

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TY - JOUR

T1 - Total synthesis of d-fagomine and 6-deoxyfagomine

AU - Min, Im Sook

AU - Kim, Seung In

AU - Hong, Seungmin

AU - Kim, In Su

AU - Jung, Young Hoon

PY - 2013/5/13

Y1 - 2013/5/13

N2 - Total synthesis of d-fagomine and 6-deoxyfagomine from readily available d-lyxose is described. The key steps included regioselective and diastereoselective amination, hydroboration-oxidation, and Appel reaction. The reaction of 3,4-anti-tribenzyl ether with chlorosulfonyl isocyanate in toluene at 0 °C afforded 3,4-anti-amino alcohol, an essential compound for the preparation of d-fagomine and 6-deoxyfagomine, with a high diastereoselectivity (dr=26:1) in 74% yield. The origin of diastereoselectivity can be explained by the neighboring group effect, which leads to retention of the stereochemistry.

AB - Total synthesis of d-fagomine and 6-deoxyfagomine from readily available d-lyxose is described. The key steps included regioselective and diastereoselective amination, hydroboration-oxidation, and Appel reaction. The reaction of 3,4-anti-tribenzyl ether with chlorosulfonyl isocyanate in toluene at 0 °C afforded 3,4-anti-amino alcohol, an essential compound for the preparation of d-fagomine and 6-deoxyfagomine, with a high diastereoselectivity (dr=26:1) in 74% yield. The origin of diastereoselectivity can be explained by the neighboring group effect, which leads to retention of the stereochemistry.

KW - Amination

KW - Chlorosulfonyl isocyanate

KW - Deoxyfagomine

KW - Fagomine

KW - Total synthesis

UR - https://www.scopus.com/pages/publications/84875930984

U2 - 10.1016/j.tet.2013.03.046

DO - 10.1016/j.tet.2013.03.046

M3 - Article

AN - SCOPUS:84875930984

SN - 0040-4020

VL - 69

SP - 3901

EP - 3906

JO - Tetrahedron

JF - Tetrahedron

IS - 19

ER -

Total synthesis of d-fagomine and 6-deoxyfagomine

Abstract

Keywords

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