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与原异麦角甾苷相关的溴代羟基蒽醌的区域定向合成。

Regiodefined synthesis of brominated hydroxyanthraquinones related to proisocrinins.

作者信息

Roy Joyeeta, Mal Tanushree, Jana Supriti, Mal Dipakranjan

机构信息

Department of Chemistry, Indian Institute of Technology, Kharagpur- 721302, India.

出版信息

Beilstein J Org Chem. 2016 Mar 16;12:531-6. doi: 10.3762/bjoc.12.52. eCollection 2016.

DOI:10.3762/bjoc.12.52
PMID:27340445
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4901998/
Abstract

Dibromobenzoisofuranone 12, synthesized in six steps, was regiospecifically annulated with 5-substituted cyclohexenones 13/36 in the presence of LiOt-Bu to give brominated anthraquinones 14/38 in good yields. Darzens condensation of 30 was shown to give chain-elongated anthraquinone 32. Alkaline hydrolysis of 38 furnished 39 representing desulfoproisocrinin F.

摘要

经六步合成的二溴苯并异呋喃酮12，在叔丁醇锂存在下与5-取代环己烯酮13/36进行区域特异性环合反应，以良好的产率得到溴代蒽醌14/38。结果表明，30的达参缩合反应生成了链延长的蒽醌32。38的碱性水解得到了代表去硫原异克菌素F的39。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3995/4901998/f3d653de4d0f/Beilstein_J_Org_Chem-12-531-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3995/4901998/6be3fe73dc50/Beilstein_J_Org_Chem-12-531-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3995/4901998/d9855e2cac72/Beilstein_J_Org_Chem-12-531-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3995/4901998/795cf9e9dd63/Beilstein_J_Org_Chem-12-531-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3995/4901998/386aa92f1f9d/Beilstein_J_Org_Chem-12-531-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3995/4901998/6667ff570cbe/Beilstein_J_Org_Chem-12-531-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3995/4901998/d2a9cd7daee0/Beilstein_J_Org_Chem-12-531-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3995/4901998/f3d653de4d0f/Beilstein_J_Org_Chem-12-531-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3995/4901998/6be3fe73dc50/Beilstein_J_Org_Chem-12-531-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3995/4901998/d9855e2cac72/Beilstein_J_Org_Chem-12-531-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3995/4901998/795cf9e9dd63/Beilstein_J_Org_Chem-12-531-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3995/4901998/386aa92f1f9d/Beilstein_J_Org_Chem-12-531-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3995/4901998/6667ff570cbe/Beilstein_J_Org_Chem-12-531-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3995/4901998/d2a9cd7daee0/Beilstein_J_Org_Chem-12-531-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3995/4901998/f3d653de4d0f/Beilstein_J_Org_Chem-12-531-g008.jpg

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