title: Traceless stereoinduction for the enantiopure synthesis of substituted-2-cyclopentenones.
abstract: The pseudoenantiomeric 4-O-Boc- and 4-OPMP-cyclopent-2-enones, readily available from hydroxymethylenefurane on multigram scale, are demonstrated to be exceptional building blocks for the synthesis of enantiopure 4-alkyl-5-(1'-hydroxyalkyl) substituted 2-cyclopentenones and derivatives thereof. The 4-OR substituent acts as a traceless stereoinducing element, conferring not only 1,2- but also 1,4-stereocontrol with excellent selectivity. The methodology developed here was applied for the rapid synthesis of natural products and biologically active 2-cyclopentenones such as TEI-9826, guaianes, and pseudoguaianolides.
authors.affiliation: Institut für Organische Chemie, Universität Regensburg , Universitätsstr. 31, 93053 Regensburg, Germany.
authors.forename: Nanaji
authors.initials: N
authors.lastname: Arisetti
authors.forename: Oliver
authors.initials: O
authors.lastname: Reiser
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D011455:Prostaglandins A, Synthetic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D045789:Sesquiterpenes, Guaiane / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; D001688:Biological Products; D003517:Cyclopentanes; D011455:Prostaglandins A, Synthetic; D045789:Sesquiterpenes, Guaiane; C469647:TEI9826; C421026:guaiane; C000595588:teuclatriol; C013905:cyclopentenone