title: Cryptocaryols A and B: total syntheses, stereochemical revision, structure elucidation, and structure-activity relationship.
abstract: The first total syntheses and structural elucidation of cryptocaryol A and cryptocaryol B were achieved in 23 and 25 linear steps, respectively. The synthesis relied on the use of a key pseudo-Cs symmetric pentaol intermediate, which in a stereochemically divergent manner was converted into either enantiomer as well as diastereomers. This synthetic effort enabled the first structure-activity relationships of this class of PDCD4 stabilizing natural products.
authors.affiliation: Department of Chemistry and Chemical Biology, Northeastern University, Boston, Massachusetts 02115, United States.
authors.forename: Yanping
authors.initials: Y
authors.lastname: Wang
authors.forename: George A
authors.initials: GA
authors.lastname: O'Doherty
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D051017:Apoptosis Regulatory Proteins / Q000037:antagonists & inhibitors* / Q000235:genetics; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D061986:MCF-7 Cells; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D016601:RNA-Binding Proteins / Q000037:antagonists & inhibitors* / Q000235:genetics; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D051017:Apoptosis Regulatory Proteins; C114487:PDCD4 protein, human; D011753:Pyrones; D016601:RNA-Binding Proteins; C585544:cryptocaryol A; C585545:cryptocaryol B