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阿霍烯(E,Z)-4,5,9-三硫杂十二-1,6,11-三烯 9-氧化物的批量和连续流(E,Z)-4,5,9-三硫杂十二-1,7,11-三烯的短全合成。

Short Total Synthesis of Ajoene, (E,Z)-4,5,9-Trithiadodeca-1,6,11-triene 9-oxide, in Batch and (E,Z)-4,5,9-Trithiadodeca-1,7,11-triene in Continuous Flow.

机构信息

School of Chemistry, Cardiff University, Park Place, Main Building, Cardiff, CF10 3AT, UK.

Neem Biotech, Roseheyworth Business Park North, Abertillery, NP13 1SX, UK.

出版信息

Chemistry. 2020 Jul 8;26(38):8363-8367. doi: 10.1002/chem.202001598. Epub 2020 Jun 15.

DOI:10.1002/chem.202001598
PMID:32364668
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7384054/
Abstract

A short total synthesis of ajoene, (E,Z)-4,5,9-trithiadodeca-1,6,11-triene 9-oxide, has been achieved over six steps. In addition, a continuous flow synthesis under mild reaction conditions to (E,Z)-4,5,9-trithiadodeca-1,7,11-triene is described starting from simple and easily accessible starting materials. Over four steps including propargylation, radical addition of thioacetate, deprotection, and disulfide formation/ allylation, the target product can be obtained at a rate of 0.26 g h in an overall yield of 12 %.

摘要

已通过六步反应实现大蒜素（E，Z）-4,5,9-三硫杂十一碳-1,6,11-三烯 9-氧化物的短总合成。此外，还描述了一种在温和反应条件下通过连续流合成（E，Z）-4,5,9-三硫杂十一碳-1,7,11-三烯的方法，起始原料简单易得。通过炔丙基化、硫代乙酸酯的自由基加成、脱保护和二硫化物形成/烯丙基化四步反应，以 0.26g/h 的速率，总收率为 12%获得目标产物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/564d/7384054/c9e20c53a1d2/CHEM-26-8363-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/564d/7384054/ae69cc43d367/CHEM-26-8363-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/564d/7384054/3b838bf0f2e8/CHEM-26-8363-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/564d/7384054/9adc1c2a6452/CHEM-26-8363-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/564d/7384054/52e98db911a0/CHEM-26-8363-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/564d/7384054/4955dc1a9cfb/CHEM-26-8363-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/564d/7384054/a5a7a4190542/CHEM-26-8363-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/564d/7384054/ec605ea6c3df/CHEM-26-8363-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/564d/7384054/c9e20c53a1d2/CHEM-26-8363-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/564d/7384054/ae69cc43d367/CHEM-26-8363-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/564d/7384054/3b838bf0f2e8/CHEM-26-8363-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/564d/7384054/9adc1c2a6452/CHEM-26-8363-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/564d/7384054/52e98db911a0/CHEM-26-8363-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/564d/7384054/4955dc1a9cfb/CHEM-26-8363-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/564d/7384054/a5a7a4190542/CHEM-26-8363-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/564d/7384054/ec605ea6c3df/CHEM-26-8363-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/564d/7384054/c9e20c53a1d2/CHEM-26-8363-g008.jpg

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本文引用的文献

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Short Total Synthesis of Ajoene.阿霍烯的短全合成。
Angew Chem Int Ed Engl. 2018 Sep 17;57(38):12290-12293. doi: 10.1002/anie.201808605. Epub 2018 Aug 19.
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An Optimized Facile Procedure to Synthesize and Purify Allicin.一种合成与纯化大蒜素的优化简便方法。
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