title: Anticancer agents from the Australian tropical rainforest: Spiroacetals EBC-23, 24, 25, 72, 73, 75 and 76.
abstract: EBC-23, 24, 25, 72, 73, 75 and 76 were isolated from the fruit of Cinnamomum laubatii (family Lauraceae) in the Australian tropical rainforests. EBC-23 (1) was synthesized stereoselectively, in nine linear steps in 8 % overall yield, to confirm the reported relative stereochemistry and determine the absolute stereochemistry. Key to the total synthesis was a series of Tietze-Smith linchpin reactions. The novel spiroacetal structural motif, exemplified by EBC-23 (1), was found to inhibit the growth of the androgen-independent prostate tumor cell line DU145 in the mouse model, indicating potential for the treatment of refractory solid tumors in adults.
authors.affiliation: School of Chemistry and Molecular Biosciences, University of Queensland, Brisbane, 4072, Queensland, Australia.
authors.forename: Lin
authors.initials: L
authors.lastname: Dong
authors.forename: Heiko
authors.initials: H
authors.lastname: Schill
authors.forename: Rebecca L
authors.initials: RL
authors.lastname: Grange
authors.forename: Achim
authors.initials: A
authors.lastname: Porzelle
authors.forename: Jenny P
authors.initials: JP
authors.lastname: Johns
authors.forename: Peter G
authors.initials: PG
authors.lastname: Parsons
authors.forename: Victoria A
authors.initials: VA
authors.lastname: Gordon
authors.forename: Paul W
authors.initials: PW
authors.lastname: Reddell
authors.forename: Craig M
authors.initials: CM
authors.lastname: Williams
mesh_terms: D000080:Acetals / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D001315:Australia; D045744:Cell Line, Tumor; D027424:Cinnamomum / Q000737:chemistry; D005638:Fruit / Q000737:chemistry; D006801:Humans; D051379:Mice; D008819:Mice, Nude; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D013237:Stereoisomerism; D023041:Xenograft Model Antitumor Assays
chemical_list: D000080:Acetals; D000970:Antineoplastic Agents; C534557:EBC-23; D011714:Pyrans; D013141:Spiro Compounds