Total Synthesis of GEX1Q1, Assignment of C-5 Stereoconfiguration and Evaluation of Spliceosome Inhibitory Activity | Zendy

Arun K. Ghosh | Zendy; Nianchun Ma | Zendy; Kerstin A. Effenberger | Zendy; Melissa S. Jurica | Zendy

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Total Synthesis of GEX1Q1, Assignment of C-5 Stereoconfiguration and Evaluation of Spliceosome Inhibitory Activity

Author(s) -

Arun K. Ghosh,

Nianchun Ma,

Kerstin A. Effenberger,

Melissa S. Jurica

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol501345d

Subject(s) - chemistry , spliceosome , total synthesis , tetrahydropyran , stereochemistry , enantioselective synthesis , ring (chemistry) , epimer , rna , biochemistry , rna splicing , organic chemistry , catalysis , gene

An enantioselective total synthesis of GEX1Q1 has been accomplished in a convergent manner. The C-5 asymmetric center has now been assigned through synthesis. GEX1Q1 displayed slightly better spliceosome inhibitory activity over its C-5 epimer. The salient features of this synthesis include an asymmetric hetero-Diels-Alder reaction to construct the tetrahydropyran ring and a Suzuki cross-coupling to assemble the key segments.

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