Formal synthesis of (±)-sedamine through gold(I)-catalyzed intramolecular dehydrative amination of sulfamate esters tethered to allylic alcohols

Yunjeong Park; Jae Sang Ryu

doi:10.1016/j.tetlet.2021.153024

Formal synthesis of (±)-sedamine through gold(I)-catalyzed intramolecular dehydrative amination of sulfamate esters tethered to allylic alcohols

Yunjeong Park, Jae Sang Ryu

Department of Pharmaceutical Sciences

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

3 Scopus citations

Abstract

A concise formal synthesis of (±)-sedamine has been accomplished. The synthesis is straightforward and demonstrates high efficiency. Key steps involve gold(I)-catalyzed cyclization of sulfamate esters tethered to allylic alcohols, sulfamate N-alkylation, and ring-closing metathesis.

Original language	English
Article number	153024
Journal	Tetrahedron Letters
Volume	71
DOIs	https://doi.org/10.1016/j.tetlet.2021.153024
State	Published - 11 May 2021

Bibliographical note

Funding Information:
This research was supported by National Research Foundation of Korea (NRF) grant funded by the Korea government ( MSIT ) ( NRF-2018R1A5A2025286 ) and ( NRF-2020R1F1A1052496 ).

Publisher Copyright:
© 2021 Elsevier Ltd

Keywords

Cyclic sulfamidate
Dehydrative amination
Gold
Sedamine
Silver

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10.1016/j.tetlet.2021.153024

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title = "Formal synthesis of (±)-sedamine through gold(I)-catalyzed intramolecular dehydrative amination of sulfamate esters tethered to allylic alcohols",

abstract = "A concise formal synthesis of (±)-sedamine has been accomplished. The synthesis is straightforward and demonstrates high efficiency. Key steps involve gold(I)-catalyzed cyclization of sulfamate esters tethered to allylic alcohols, sulfamate N-alkylation, and ring-closing metathesis.",

keywords = "Cyclic sulfamidate, Dehydrative amination, Gold, Sedamine, Silver",

author = "Yunjeong Park and Ryu, \{Jae Sang\}",

note = "Funding Information: This research was supported by National Research Foundation of Korea (NRF) grant funded by the Korea government ( MSIT ) ( NRF-2018R1A5A2025286 ) and ( NRF-2020R1F1A1052496 ). Publisher Copyright: {\textcopyright} 2021 Elsevier Ltd",

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AU - Park, Yunjeong

AU - Ryu, Jae Sang

N1 - Funding Information: This research was supported by National Research Foundation of Korea (NRF) grant funded by the Korea government ( MSIT ) ( NRF-2018R1A5A2025286 ) and ( NRF-2020R1F1A1052496 ). Publisher Copyright: © 2021 Elsevier Ltd

PY - 2021/5/11

Y1 - 2021/5/11

N2 - A concise formal synthesis of (±)-sedamine has been accomplished. The synthesis is straightforward and demonstrates high efficiency. Key steps involve gold(I)-catalyzed cyclization of sulfamate esters tethered to allylic alcohols, sulfamate N-alkylation, and ring-closing metathesis.

AB - A concise formal synthesis of (±)-sedamine has been accomplished. The synthesis is straightforward and demonstrates high efficiency. Key steps involve gold(I)-catalyzed cyclization of sulfamate esters tethered to allylic alcohols, sulfamate N-alkylation, and ring-closing metathesis.

KW - Cyclic sulfamidate

KW - Dehydrative amination

KW - Gold

KW - Sedamine

KW - Silver

UR - https://www.scopus.com/pages/publications/85103734545

U2 - 10.1016/j.tetlet.2021.153024

DO - 10.1016/j.tetlet.2021.153024

M3 - Article

AN - SCOPUS:85103734545

SN - 0040-4039

VL - 71

JO - Tetrahedron Letters

JF - Tetrahedron Letters

M1 - 153024

ER -

Formal synthesis of (±)-sedamine through gold(I)-catalyzed intramolecular dehydrative amination of sulfamate esters tethered to allylic alcohols

Abstract

Bibliographical note

Keywords

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