title: Lasonolide A: structural revision and total synthesis.
abstract: The proposed structure of lasonolide A was synthesized employing radical cyclization reactions of beta-alkoxyacrylates for preparation of the tetrahydropyranyl units A and B, but the spectroscopic data did not match those of the natural product. Both enantiomers of a revised structure featuring 17E,25Z double bonds were synthesized, and the (-)-isomer was found to be the biologically active enantiomer.
authors.affiliation: School of Chemistry and Molecular Engineering, Seoul National University, Seoul 151-747, Korea.
authors.forename: Ho Young
authors.initials: HY
authors.lastname: Song
authors.forename: Jung Min
authors.initials: JM
authors.lastname: Joo
authors.forename: Jung Won
authors.initials: JW
authors.lastname: Kang
authors.forename: Dae-Shik
authors.initials: DS
authors.lastname: Kim
authors.forename: Cheol-Kyu
authors.initials: CK
authors.lastname: Jung
authors.forename: Hyo Shin
authors.initials: HS
authors.lastname: Kwak
authors.forename: Jin Hyun
authors.initials: JH
authors.lastname: Park
authors.forename: Eun
authors.initials: E
authors.lastname: Lee
authors.forename: Chang Yong
authors.initials: CY
authors.lastname: Hong
authors.forename: ShinWu
authors.initials: S
authors.lastname: Jeong
authors.forename: Kiwan
authors.initials: K
authors.lastname: Jeon
authors.forename: Ji Hyun
authors.initials: JH
authors.lastname: Park
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002455:Cell Division / Q000187:drug effects; D003500:Cyclization; D006801:Humans; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
chemical_list: D000970:Antineoplastic Agents; D018942:Macrolides; C450700:lasonolide A