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通过悬垂硅醇开环氮丙啶可制备(±)-克拉维醇 H、(±)-去乙酰克拉维醇 H、(±)-二氢神经鞘氨醇和(±)-己酰基二氢神经鞘氨醇。

Ring Opening of Aziridines by Pendant Silanols Allows for Preparations of (±)-Clavaminol H, (±)-Des-Acetyl-Clavaminol H, (±)-Dihydrosphingosine, and (±)--Hexanoyldihydrosphingosine.

机构信息

Department of Medicinal Chemistry, University of Kansas, Lawrence, Kansas 66045, United States.

Department of Chemistry, Tulane University, New Orleans, Louisiana 70118, United States.

出版信息

Org Lett. 2022 Aug 26;24(33):6202-6207. doi: 10.1021/acs.orglett.2c02496. Epub 2022 Aug 11.

DOI:10.1021/acs.orglett.2c02496
PMID:35951966
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10017055/
Abstract

We present a unique strategy for the synthesis of vicinal amino alcohols. Ring opening of aziridines with pendant silanols is compatible with a range of substrates. To engage productively in ring opening, the aziridine must be at least mildly activated, and a variety of such -substituents are tolerated. The utility of this methodology is highlighted in facile preparations of the natural products (±)-Clavaminol H, (±)-dihydrosphingosine, and (±)--hexanoyldihydrosphingosine as well as a natural product analogue (±)-des-acetyl-Clavaminol H.

摘要

我们提出了一种独特的合成偕氨基醇的策略。氮丙啶与侧链硅醇的开环反应与一系列底物兼容。为了有效地进行开环反应，氮丙啶必须至少被轻度活化，并且可以容忍各种这样的取代基。该方法的实用性在天然产物（±）-Clavaminol H、（±）-dihydrosphingosine 和（±）--hexanoyldihydrosphingosine 以及天然产物类似物（±）-des-acetyl-Clavaminol H 的简便制备中得到了很好的体现。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b722/10017055/4c5de11b508c/nihms-1880565-f0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b722/10017055/b0c94a3b2859/nihms-1880565-f0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b722/10017055/00200e2fffd4/nihms-1880565-f0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b722/10017055/30b2f9a597d0/nihms-1880565-f0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b722/10017055/dba1f2fb107e/nihms-1880565-f0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b722/10017055/7f1812879dbd/nihms-1880565-f0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b722/10017055/4c5de11b508c/nihms-1880565-f0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b722/10017055/b0c94a3b2859/nihms-1880565-f0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b722/10017055/00200e2fffd4/nihms-1880565-f0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b722/10017055/30b2f9a597d0/nihms-1880565-f0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b722/10017055/dba1f2fb107e/nihms-1880565-f0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b722/10017055/7f1812879dbd/nihms-1880565-f0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b722/10017055/4c5de11b508c/nihms-1880565-f0007.jpg

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Ring Opening of Aziridines by Pendant Silanols Allows for Preparations of (±)-Clavaminol H, (±)-Des-Acetyl-Clavaminol H, (±)-Dihydrosphingosine, and (±)--Hexanoyldihydrosphingosine.通过悬垂硅醇开环氮丙啶可制备(±)-克拉维醇 H、(±)-去乙酰克拉维醇 H、(±)-二氢神经鞘氨醇和(±)-己酰基二氢神经鞘氨醇。
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