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
 
Publication type: Journal Article
Publication date: 2025-02-19
Georg Thieme Verlag KG
scimago Q3
wos Q3
SJR: 0.437
CiteScore: 3.3
Impact factor: 1.4
ISSN: 09365214, 14372096
Abstract

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.
GOST all authors (up to 50) Copy
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}
}