Total synthesis of aloin via regioselective Diels–Alder reactions connecting two 3-silylbenzynes and 2-stannylfuran

Shuji Akai 1, 2, 3
, 
Shogo Moriyama 1, 2
, 
Yuto Emi 1, 2
, 
Toshifumi Nosaki 3, 4
, 
Yuki MORIKAWA 3, 4
, 
Takashi Shigeta 3, 5, 6
, 
Akira Takagi 7, 8
, 
Masahiro Egi 3, 4, 6
, 
Takashi Ikawa 2, 3, 9, 10
, 
Yoshinari Sawama 1, 2
1
 
2
 
3
 
4
 
5
 
6
 
7
 
Pharmaceutical Sciences, Kobe Yakka Daigaku, Kobe, Japan | 
8
 
9
 
10
 
Тип публикации: Journal Article
Дата публикации: 2025-02-19
Georg Thieme Verlag KG
scimago Q3
wos Q3
БС2
SJR: 0.437
CiteScore: 3.3
Impact factor: 1.4
ISSN: 09365214, 14372096
Краткое описание

The first synthesis of aloin, a natural anthrone C-glycoside, was achieved through two sequential Diels–Alder (DA) reactions connecting two 3-silylbenzynes and a 2-stannylfuran. The silyl and stannyl substituents contributed to the regioselectivity of the two DA reactions and the 9,10-ether cleavage of the DA adduct. Subsequent conversion of the silyl groups into hydroxy groups and a C10-glycosylation completed the synthesis of aloin.

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Moriyama S. et al. Total synthesis of aloin via regioselective Diels–Alder reactions connecting two 3-silylbenzynes and 2-stannylfuran // Synlett. 2025.
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Akai S., Moriyama S., Emi Y., Nosaki T., MORIKAWA Y., Shigeta T., Takagi A., Egi M., Ikawa T., Sawama Y. Total synthesis of aloin via regioselective Diels–Alder reactions connecting two 3-silylbenzynes and 2-stannylfuran // Synlett. 2025.
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TY - JOUR
DO - 10.1055/a-2542-3481
UR - http://www.thieme-connect.de/DOI/DOI?10.1055/a-2542-3481
TI - Total synthesis of aloin via regioselective Diels–Alder reactions connecting two 3-silylbenzynes and 2-stannylfuran
T2 - Synlett
AU - Akai, Shuji
AU - Moriyama, Shogo
AU - Emi, Yuto
AU - Nosaki, Toshifumi
AU - MORIKAWA, Yuki
AU - Shigeta, Takashi
AU - Takagi, Akira
AU - Egi, Masahiro
AU - Ikawa, Takashi
AU - Sawama, Yoshinari
PY - 2025
DA - 2025/02/19
PB - Georg Thieme Verlag KG
SN - 0936-5214
SN - 1437-2096
ER -
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@article{2025_Moriyama,
author = {Shuji Akai and Shogo Moriyama and Yuto Emi and Toshifumi Nosaki and Yuki MORIKAWA and Takashi Shigeta and Akira Takagi and Masahiro Egi and Takashi Ikawa and Yoshinari Sawama},
title = {Total synthesis of aloin via regioselective Diels–Alder reactions connecting two 3-silylbenzynes and 2-stannylfuran},
journal = {Synlett},
year = {2025},
publisher = {Georg Thieme Verlag KG},
month = {feb},
url = {http://www.thieme-connect.de/DOI/DOI?10.1055/a-2542-3481},
doi = {10.1055/a-2542-3481}
}