title: Total synthesis and preliminary biological evaluation of cis-solamin isomers.
abstract: An efficient total synthesis of cis-solamin (1) has been achieved in 21% overall yield and with a longest linear sequence of just 11 steps from aldehyde 8. A key feature of the approach was the use of asymmetric permanganate-promoted oxidative cyclization to introduce four of the five required stereocenters in a single step. The use of robust and chemoselective methodology meant that the use of protecting groups could be avoided during the assembly of cis-solamin (1) from the three fragments 23, 6, and 4. The methodology was also applied to the synthesis of three further cis-solamin isomers 2, ent-1, and ent-2. Cytotoxicity and hemolytic properties of cis-solamin isomers and synthetic intermediates are reported.
authors.affiliation: Department of Chemistry, The University of Southampton, Highfield, UK.
authors.forename: Alex R L
authors.initials: AR
authors.lastname: Cecil
authors.forename: Yulai
authors.initials: Y
authors.lastname: Hu
authors.forename: María J
authors.initials: MJ
authors.lastname: Vicent
authors.forename: Ruth
authors.initials: R
authors.lastname: Duncan
authors.forename: Richard C D
authors.initials: RC
authors.lastname: Brown
mesh_terms: D000818:Animals; D001558:Benzethonium / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D003500:Cyclization; D004852:Epoxy Compounds / Q000138:chemical synthesis; D020128:Inhibitory Concentration 50; D007536:Isomerism; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: D004852:Epoxy Compounds; D001558:Benzethonium