Unknown

Dataset Information

0

Efficient access to sp3-rich tricyclic amine scaffolds through Diels-Alder reactions of azide-containing silyloxydienes.


ABSTRACT: The preparation of sp3-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 sp3 carbon centers.

SUBMITTER: McLeod MC 

PROVIDER: S-EPMC4957953 | biostudies-literature | 2016 Jun

REPOSITORIES: biostudies-literature

altmetric image

Publications

Efficient access to sp<sup>3</sup>-rich tricyclic amine scaffolds through Diels-Alder reactions of azide-containing silyloxydienes.

McLeod Michael C MC   Aubé Jeffrey J  

Tetrahedron 20160601 26


The preparation of sp<sup>3</sup>-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 compo  ...[more]

Similar Datasets

| S-EPMC3458765 | biostudies-other
| S-EPMC9400981 | biostudies-literature
| S-EPMC6521805 | biostudies-literature
| S-EPMC4045115 | biostudies-literature
| S-EPMC6771859 | biostudies-literature
| S-EPMC2912946 | biostudies-literature
| S-EPMC7187354 | biostudies-literature
| S-EPMC9087347 | biostudies-literature
| S-EPMC1399462 | biostudies-literature
| S-EPMC7154774 | biostudies-literature