title: Total synthesis of Δ¹²-prostaglandin J₃, a highly potent and selective antileukemic agent.
abstract: A catalytic asymmetric total synthesis of the potent and selective antileukemic Δ(12)-prostaglandin J3 (Δ(12)-PGJ3) is described. The convergent synthesis proceeded through intermediates 2 and 3, formed enantioselectively from readily available starting materials and coupled through an aldol reaction followed by dehydration to afford stereoselectively the cyclopentenone alkylidene structural motif of the molecule.
authors.affiliation: Department of Chemistry, BioScience Research Collaborative, Rice University, 6100 Main Street, Houston, TX 77005 (USA). kcn@rice.edu.
authors.forename: K C
authors.initials: KC
authors.lastname: Nicolaou
authors.forename: Philipp
authors.initials: P
authors.lastname: Heretsch
authors.forename: Abdelatif
authors.initials: A
authors.lastname: ElMarrouni
authors.forename: Christopher R H
authors.initials: CR
authors.lastname: Hale
authors.forename: Kiran K
authors.initials: KK
authors.lastname: Pulukuri
authors.forename: Avinash K
authors.initials: AK
authors.lastname: Kudva
authors.forename: Vivek
authors.initials: V
authors.lastname: Narayan
authors.forename: K Sandeep
authors.initials: KS
authors.lastname: Prabhu
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003517:Cyclopentanes / Q000737:chemistry; D015525:Fatty Acids, Omega-3 / Q000138:chemical synthesis* / Q000737:chemistry; D011453:Prostaglandins / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000970:Antineoplastic Agents; D003517:Cyclopentanes; D015525:Fatty Acids, Omega-3; D011453:Prostaglandins; C570766:delta12-prostaglandin J3; C116609:3-hydroxybutanal; D012238:Rhodium; C013905:cyclopentenone
keywords: CH activation; asymmetric catalysis; leukemia; natural products; total synthesis
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