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帕尔那芬净中异恶唑并[4,3,2 - de]菲啶酮部分的合成

Synthesis of the isoxazolo[4,3,2-de]phenanthridinone moiety of the parnafungins.

作者信息

Zhou Quan, Snider Barry B

机构信息

Department of Chemistry, MS 015, Brandeis University, Waltham, Massachusetts 02454-9110, USA.

出版信息

Org Lett. 2009 Jul 2;11(13):2936-9. doi: 10.1021/ol901054r.

DOI:10.1021/ol901054r
PMID:19496595
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2760249/
Abstract

A practical route to the labile tetracyclic isoxazolo[4,3,2-de]phenanthridinone moiety of the antifungal parnafungins has been developed. Zinc reduction of a methyl 2'-hydroxymethyl-2-nitro-3-biphenylcarboxylate, which was prepared by a Suzuki coupling, afforded a benzisoxazolone that was treated with MsCl and base to generate the labile tetracyclic ring system in 37-47% yield. This compound decomposes to the phenanthridine in CDCl(3) and the phenanthridine N-oxide in aqueous base.

摘要

已开发出一条制备抗真菌药物帕尔那芬净中不稳定的四环异恶唑并[4,3,2 - de]菲啶酮部分的实用路线。通过铃木偶联反应制备的2'-羟甲基-2-硝基-3-联苯羧酸甲酯经锌还原，得到一种苯并异恶唑酮，该苯并异恶唑酮用甲磺酰氯和碱处理，以37 - 47%的产率生成不稳定的四环环系。该化合物在CDCl₃中分解为菲啶，在碱性水溶液中分解为菲啶N-氧化物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7bc7/2760249/a31adf2fff99/nihms-149393-f0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7bc7/2760249/a9e4d9c53896/nihms-149393-f0002.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7bc7/2760249/82aa0b342b84/nihms-149393-f0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7bc7/2760249/c41cd8773cb9/nihms-149393-f0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7bc7/2760249/29a7ccbd0155/nihms-149393-f0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7bc7/2760249/bd99bc7500c2/nihms-149393-f0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7bc7/2760249/eea4c10daea5/nihms-149393-f0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7bc7/2760249/a31adf2fff99/nihms-149393-f0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7bc7/2760249/a9e4d9c53896/nihms-149393-f0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7bc7/2760249/ecb36418d1c1/nihms-149393-f0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7bc7/2760249/82aa0b342b84/nihms-149393-f0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7bc7/2760249/c41cd8773cb9/nihms-149393-f0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7bc7/2760249/29a7ccbd0155/nihms-149393-f0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7bc7/2760249/bd99bc7500c2/nihms-149393-f0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7bc7/2760249/eea4c10daea5/nihms-149393-f0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7bc7/2760249/a31adf2fff99/nihms-149393-f0009.jpg

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