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用于合成类似于栗精胺的多羟基化3-甲基中氮茚的多米诺格氏加成/Cope-霍斯反应

Domino Grignard Addition/Cope-House Reaction for the Synthesis of Polyhydroxylated 3-Methylindolizidines Analogous to Castanospermine.

作者信息

Lulli Thomas, Dei Filippo, Martínez-Bailén Macarena, Matassini Camilla, Faggi Cristina, Cardona Francesca, Goti Andrea

机构信息

Dipartimento di Chimica 'Ugo Schiff' (DICUS), Università di Firenze, via della Lastruccia 3-13, 50019 Sesto Fiorentino (FI), Italy.

出版信息

Org Lett. 2025 Sep 12;27(36):10098-10104. doi: 10.1021/acs.orglett.5c03187. Epub 2025 Sep 2.

DOI:10.1021/acs.orglett.5c03187
PMID:40891620
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12442074/
Abstract

The first synthesis of polyhydroxylated 3-methylindolizidines is reported. A straightforward domino butenylmagnesium bromide addition/Cope-House reaction to carbohydrate-derived nitrones afforded efficiently the methyl pyrrolidine moiety with good stereoselectivity, which can be reversed by use of Lewis acids. A subsequent one-pot deprotection/deoxygenation/reductive amination step furnished the desired bicyclic architecture, allowing us to afford the desired final products in 3-4 steps from the starting nitrones and 18-30% overall yields.

摘要

报道了多羟基化3-甲基吲哚嗪的首次合成。对碳水化合物衍生的硝酮进行直接的多米诺溴化丁烯基镁加成/Cope-House反应，能以良好的立体选择性高效地得到甲基吡咯烷部分，使用路易斯酸可使其反转。随后的一锅法脱保护/脱氧/还原胺化步骤提供了所需的双环结构，使我们能够从起始硝酮通过3至4步反应得到所需的最终产物，总收率为18 - 30%。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e11b/12442074/39742fd9fba2/ol5c03187_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e11b/12442074/7b214168c9d4/ol5c03187_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e11b/12442074/2fc10c328e82/ol5c03187_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e11b/12442074/debf33e4e808/ol5c03187_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e11b/12442074/58599214e722/ol5c03187_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e11b/12442074/ad33a7332410/ol5c03187_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e11b/12442074/39742fd9fba2/ol5c03187_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e11b/12442074/7b214168c9d4/ol5c03187_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e11b/12442074/2fc10c328e82/ol5c03187_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e11b/12442074/debf33e4e808/ol5c03187_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e11b/12442074/58599214e722/ol5c03187_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e11b/12442074/ad33a7332410/ol5c03187_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e11b/12442074/39742fd9fba2/ol5c03187_0006.jpg

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本文引用的文献

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C-2 fluorinated castanospermines as potent and specific α-glucosidase inhibitors: synthesis and structure-activity relationship study.C-2 氟化栗精胺作为强效且特异性的α-葡萄糖苷酶抑制剂：合成及构效关系研究
Org Biomol Chem. 2025 Mar 19;23(12):2854-2877. doi: 10.1039/d4ob01542h.
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Synthesis of 2-hydroxy analogues of castanospermine, 1-epi-castanospermine and their iminooctitols from sugar-derived lactam.从糖衍生的内酰胺合成栗精胺、1-表栗精胺及其亚氨基辛糖醇的2-羟基类似物。
Carbohydr Res. 2025 Apr;550:109385. doi: 10.1016/j.carres.2025.109385. Epub 2025 Jan 14.
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Castanospermine suppresses CD44 ectodomain cleavage as revealed by transmembrane bioluminescent sensors.
通过跨膜生物发光传感器发现，栗精胺可抑制CD44胞外域裂解。
J Cell Sci. 2022 Mar 15;135(6). doi: 10.1242/jcs.259314. Epub 2022 Mar 17.
4
Inhibitors of Protein Glycosylation Are Active against the Coronavirus Severe Acute Respiratory Syndrome Coronavirus SARS-CoV-2.蛋白质糖基化抑制剂对冠状病毒严重急性呼吸综合征冠状病毒2（SARS-CoV-2）具有活性。
Viruses. 2021 Apr 30;13(5):808. doi: 10.3390/v13050808.
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Biologically active indolizidine alkaloids.具有生物活性的吲哚里西啶生物碱。
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Glycobiology. 2021 May 3;31(4):378-384. doi: 10.1093/glycob/cwaa091.
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