Efficient access to sp 3 -rich tricyclic amine scaffolds through Diels-Alder reactions of azide-containing silyloxydienes
The preparation of sp -rich scaffolds to obtain more natural product-like libraries for incorporation into screening decks is challenging. Here, we describe the use of a Diels-Alder reaction between an enone and an azide-containing silyloxydiene to gain efficient access to complex tricyclic amine sc...
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| Veröffentlicht in: | Tetrahedron 2016-06, Vol.72 (26), p.3766 |
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| container_title | Tetrahedron |
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| creator | McLeod, Michael C Aubé, Jeffrey |
| description | The preparation of sp
-rich scaffolds to obtain more natural product-like libraries for incorporation into screening decks is challenging. Here, we describe the use of a Diels-Alder reaction between an enone and an azide-containing silyloxydiene to gain efficient access to complex tricyclic amine scaffolds. Derivatization of these scaffolds provided a library of 80 amines, amides, sulfonamides, quinolines and indolenines, all in >20 mg quantities and >90% purities. These library compounds displayed properties more similar to alkaloid natural products than to drugs and commercial drug-like libraries, as shown by a high proportion of sp
carbon centers. |
| format | Article |
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| ispartof | Tetrahedron, 2016-06, Vol.72 (26), p.3766 |
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| language | eng |
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| source | Elsevier ScienceDirect Journals |
| title | Efficient access to sp 3 -rich tricyclic amine scaffolds through Diels-Alder reactions of azide-containing silyloxydienes |
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