Synthesis of (S)-jamaicamide C carboxylic acid.
The jamaicamides are natural product sodium channel blockers derived from the cyanobacterium Lyngbya majuscula. The carboxylic acid fragment of jamaicamide C contains a methyl stereocenter and a trisubstituted E chloroolefin. Herein, we present the nonracemic synthesis of the aliphatic chain of jamaicamide C. The methyl stereocenter was installed using Evans' oxazolidinone methodology, and the trisubstituted chloroolefin was set by silylstannylation of a triple bond.
Graf
Kristin M
KM
Department of Chemistry, University of Virginia, McCormick Road, Charlottesville, Virginia 22901, USA.
Tabor
Martin G
MG
Brown
Milton L
ML
Paige
Mikell
M
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D055666:Lipopeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008235:Lyngbya Toxins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D011760:Pyrrolidinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D026941:Sodium Channel Blockers / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
D000577:Amides; D001688:Biological Products; D002264:Carboxylic Acids; D055666:Lipopeptides; D008235:Lyngbya Toxins; D011760:Pyrrolidinones; D026941:Sodium Channel Blockers; C494605:jamaicamide C