Total synthesis of chromanol 293B and cromakalim via stereoselective amination of chiral benzylic ethers

Sang Ho Ma; Yeon Su Kim; Jun Min Jung; Pulla Reddy Boggu; Seung Chan Kim; In Su Kim; Young Hoon Jung

doi:10.1016/j.tetlet.2019.151431

Total synthesis of chromanol 293B and cromakalim via stereoselective amination of chiral benzylic ethers

Sang Ho Ma
, Yeon Su Kim
, Jun Min Jung
, Pulla Reddy Boggu
, Seung Chan Kim
, In Su Kim
, Young Hoon Jung

Department of Pharmacy

Sungkyunkwan University

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

7 Scopus citations

Abstract

Stereoselective benzylic amination reaction is important for their further application as pharmaceuticals and agrochemicals, and other chemical entities. Herein, we describe the diastereoselective amination of 1,2-anti-dialkoxychromane on chromane framework using chlorosulfonyl isocyanate. Notably, the utility of this protocol is highlighted by the total synthesis of chromanol 293B and cromakalim.

Original language	English
Article number	151431
Journal	Tetrahedron Letters
Volume	61
Issue number	5
DOIs	https://doi.org/10.1016/j.tetlet.2019.151431
State	Published - 30 Jan 2020

Keywords

Amination
Chlorosulfonyl isocyanate
Chromanol
Cromakalim
Total synthesis

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10.1016/j.tetlet.2019.151431

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title = "Total synthesis of chromanol 293B and cromakalim via stereoselective amination of chiral benzylic ethers",

abstract = "Stereoselective benzylic amination reaction is important for their further application as pharmaceuticals and agrochemicals, and other chemical entities. Herein, we describe the diastereoselective amination of 1,2-anti-dialkoxychromane on chromane framework using chlorosulfonyl isocyanate. Notably, the utility of this protocol is highlighted by the total synthesis of chromanol 293B and cromakalim.",

keywords = "Amination, Chlorosulfonyl isocyanate, Chromanol, Cromakalim, Total synthesis",

author = "Ma, \{Sang Ho\} and Kim, \{Yeon Su\} and Jung, \{Jun Min\} and Boggu, \{Pulla Reddy\} and Kim, \{Seung Chan\} and Kim, \{In Su\} and Jung, \{Young Hoon\}",

note = "Publisher Copyright: {\textcopyright} 2019 Elsevier Ltd",

year = "2020",

month = jan,

day = "30",

doi = "10.1016/j.tetlet.2019.151431",

language = "English",

volume = "61",

journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Total synthesis of chromanol 293B and cromakalim via stereoselective amination of chiral benzylic ethers

AU - Ma, Sang Ho

AU - Kim, Yeon Su

AU - Jung, Jun Min

AU - Boggu, Pulla Reddy

AU - Kim, Seung Chan

AU - Kim, In Su

AU - Jung, Young Hoon

PY - 2020/1/30

Y1 - 2020/1/30

N2 - Stereoselective benzylic amination reaction is important for their further application as pharmaceuticals and agrochemicals, and other chemical entities. Herein, we describe the diastereoselective amination of 1,2-anti-dialkoxychromane on chromane framework using chlorosulfonyl isocyanate. Notably, the utility of this protocol is highlighted by the total synthesis of chromanol 293B and cromakalim.

AB - Stereoselective benzylic amination reaction is important for their further application as pharmaceuticals and agrochemicals, and other chemical entities. Herein, we describe the diastereoselective amination of 1,2-anti-dialkoxychromane on chromane framework using chlorosulfonyl isocyanate. Notably, the utility of this protocol is highlighted by the total synthesis of chromanol 293B and cromakalim.

KW - Amination

KW - Chlorosulfonyl isocyanate

KW - Chromanol

KW - Cromakalim

KW - Total synthesis

UR - https://www.scopus.com/pages/publications/85078580518

U2 - 10.1016/j.tetlet.2019.151431

DO - 10.1016/j.tetlet.2019.151431

M3 - Article

AN - SCOPUS:85078580518

SN - 0040-4039

VL - 61

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 5

M1 - 151431

ER -

Total synthesis of chromanol 293B and cromakalim via stereoselective amination of chiral benzylic ethers

Abstract

Keywords

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