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Synlett
DOI: 10.1055/a-2542-3481
letter

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

Shogo Moriyama
1   Graduate School of Pharmaceutical Sciences, Osaka University, Suita, Japan (Ringgold ID: RIN13013)
,
Yuto Emi
1   Graduate School of Pharmaceutical Sciences, Osaka University, Suita, Japan (Ringgold ID: RIN13013)
,
Toshifumi Nosaki
2   School of Pharmaceutical Sciences, University of Shizuoka, Shizuoka, Japan (Ringgold ID: RIN13140)
,
Yuki Morikawa
2   School of Pharmaceutical Sciences, University of Shizuoka, Shizuoka, Japan (Ringgold ID: RIN13140)
,
Takashi Shigeta 
3   Graduate School of Integrated Pharmaceutical and Nutritional Sciences, University of Shizuoka, Shizuoka, Japan (Ringgold ID: RIN13140)
,
Akira Takagi
4   Pharmaceutical Sciences, Kobe Yakka Daigaku, Kobe, Japan (Ringgold ID: RIN12883)
,
Masahiro Egi 
5   School of Pharmaceutical Sciences, University of Shizuoka, Shizuoka, Japan
,
Takashi Ikawa
6   School of Pharmaceutical Sciences, Gifu Pharmaceutical University, Gifu, Japan (Ringgold ID: RIN12784)
,
Yoshinari Sawama 
7   Graduate School of Pharmaceutical Sciences, Osaka University, Suita, Japan
,
Shuji Akai 
1   Graduate School of Pharmaceutical Sciences, Osaka University, Suita, Japan (Ringgold ID: RIN13013)
› Author AffiliationsSupported by: Japan Agency for Medical Research and Development JP24ama121054
Supported by: Japan Science and Technology Agency JPMJSP2138
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The first synthesis of aloin, a natural anthrone C-glycoside, was achieved via two sequential Diels–Alder (DA) reactions connecting 3-silyl-benzynes and 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. The subsequent conversion of silyl groups to hydroxyl groups and C10-glycosylation completed the synthesis of aloin.



Publication History

Received: 29 December 2024

Accepted after revision: 19 February 2025

Accepted Manuscript online:
19 February 2025

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