Synthesis of cis-solamin using a permanganate-mediated oxidative cyclization.
[reaction: see text] cis-Solamin (1) and its diastereoisomer 14 have been synthesized in 13 steps using the diastereoselective permanganate-promoted oxidative cyclization of 1,5-dienes to create the tetrahydrofuran diol core. Notably, no protecting groups are required during the stages of fragment assembly.
Cecil
Alexander R L
AR
Department of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK.
Brown
Richard C D
RC
D001558:Benzethonium / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D011196:Potassium Permanganate / Q000737:chemistry*
D011196:Potassium Permanganate; D001558:Benzethonium