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通过无金属叔丁基过氧化氢促进的2-（氨基甲基）联苯氧化环化反应合成高度取代的芴酮。及其在诺比酮全合成中的应用。

Synthesis of highly substituted fluorenones via metal-free TBHP-promoted oxidative cyclization of 2-(aminomethyl)biphenyls. Application to the total synthesis of nobilone.

作者信息

Jourjine Ilya A P, Zeisel Lukas, Krauß Jürgen, Bracher Franz

机构信息

Department of Pharmacy - Center for Drug Research, Ludwig-Maximilians University of Munich, Butenandtstraße 5-13, 81377 Munich, Germany.

出版信息

Beilstein J Org Chem. 2021 Nov 2;17:2668-2679. doi: 10.3762/bjoc.17.181. eCollection 2021.

DOI:10.3762/bjoc.17.181
PMID:34804239
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8576822/
Abstract

Highly substituted fluorenones are readily prepared in mostly fair to good yields via metal- and additive-free TBHP-promoted cross-dehydrogenative coupling (CDC) of readily accessible -methyl-2-(aminomethyl)biphenyls and 2-(aminomethyl)biphenyls. This methodology is compatible with numerous functional groups (methoxy, cyano, nitro, chloro, and SEM and TBS-protective groups for phenols) and was further utilized in the first total synthesis of the natural product nobilone.

摘要

通过易于获得的α-甲基-2-（氨基甲基）联苯和2-（氨基甲基）联苯的无金属和添加剂的叔丁基过氧化氢促进的交叉脱氢偶联（CDC）反应，可以很容易地以大多中等至良好的产率制备高度取代的芴酮。该方法与许多官能团（甲氧基、氰基、硝基、氯以及用于酚类的SEM和TBS保护基团）兼容，并进一步用于天然产物诺比隆的首次全合成。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1732/8576822/7d4278888321/Beilstein_J_Org_Chem-17-2668-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1732/8576822/9930a00bed50/Beilstein_J_Org_Chem-17-2668-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1732/8576822/4f25ae278c3f/Beilstein_J_Org_Chem-17-2668-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1732/8576822/a4529fcd10a3/Beilstein_J_Org_Chem-17-2668-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1732/8576822/7aa90ba4ba51/Beilstein_J_Org_Chem-17-2668-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1732/8576822/a7da9653a4d5/Beilstein_J_Org_Chem-17-2668-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1732/8576822/9de48685a88f/Beilstein_J_Org_Chem-17-2668-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1732/8576822/ef62d609ed36/Beilstein_J_Org_Chem-17-2668-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1732/8576822/7d4278888321/Beilstein_J_Org_Chem-17-2668-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1732/8576822/9930a00bed50/Beilstein_J_Org_Chem-17-2668-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1732/8576822/4f25ae278c3f/Beilstein_J_Org_Chem-17-2668-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1732/8576822/a4529fcd10a3/Beilstein_J_Org_Chem-17-2668-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1732/8576822/7aa90ba4ba51/Beilstein_J_Org_Chem-17-2668-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1732/8576822/a7da9653a4d5/Beilstein_J_Org_Chem-17-2668-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1732/8576822/9de48685a88f/Beilstein_J_Org_Chem-17-2668-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1732/8576822/ef62d609ed36/Beilstein_J_Org_Chem-17-2668-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1732/8576822/7d4278888321/Beilstein_J_Org_Chem-17-2668-g009.jpg

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