title: Total synthesis of GEX1Q1, assignment of C-5 stereoconfiguration and evaluation of spliceosome inhibitory activity.
abstract: 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.
authors.affiliation: Department of Chemistry and Department of Medicinal Chemistry, Purdue University , 560 Oval Drive, West Lafayette, Indiana 47907, United States.
authors.forename: Arun K
authors.initials: AK
authors.lastname: Ghosh
authors.forename: Nianchun
authors.initials: N
authors.lastname: Ma
authors.forename: Kerstin A
authors.initials: KA
authors.lastname: Effenberger
authors.forename: Melissa S
authors.initials: MS
authors.lastname: Jurica
mesh_terms: D061565:Cycloaddition Reaction; D005233:Fatty Alcohols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D018942:Macrolides; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D017381:Spliceosomes; D013237:Stereoisomerism
chemical_list: D005233:Fatty Alcohols; D018942:Macrolides; D011714:Pyrans; C076087:herboxidiene