Total Synthesis of Aloin by Regioselective Diels-Alder Reactions Connecting Two 3-Silylbenzynes and a 2-Stannylfuran

被引：0

作者：

Moriyama, Shogo ^{[1
]}

Emi, Yuto ^{[1
]}

Nosaki, Toshifumi ^{[2
]}

Morikawa, Yuki ^{[2
]}

Shigeta, Takashi ^{[2
,3
]}

Takagi, Akira ^{[4
]}

Egi, Masahiro ^{[2
,3
]}

Ikawa, Takashi ^{[1
,2
,5
]}

Sawama, Yoshinari ^{[1
]}

Akai, Shuji ^{[1
,2
]}

机构：

[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

[2] Univ Shizuoka, Sch Pharmaceut Sci, Suruga Ku, Shizuoka, Shizuoka 4228526, Japan

[3] Univ Shizuoka, Sch Food & Nutr Sci, Suruga Ku, Shizuoka, Shizuoka 4228526, Japan

[4] Kobe Pharmaceut Univ, Higashinada Ku, Kobe, Hyogo 6588558, Japan

[5] Gifu Pharmaceut Univ, Gifu, Gifu 5011196, Japan

来源：

SYNLETT | 2025年 / 36卷 / 10期

关键词：

total synthesis; aloin; Diels-Alder reaction; benzynes; stannylfurans; glycosylation; ANTHRAQUINONES; GENERATION; CYCLOADDITION; DERIVATIVES; EMODIN; ATE;

D O I：

10.1055/a-2542-3481

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：1413 / 1417

页数：5

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