Total synthesis of cis-solamin: exploiting the RuO4-catalyzed oxidative cyclization of dienes.
[structure: see text] An enantioselective total synthesis of cis-solamin has been accomplished using a highly diastereoselective ruthenium tetroxide catalyzed oxidative cyclization as a crucial transformation. Further key steps involved an enzymatic desymmetrization, a TPAP-catalyzed oxidative termini differentiation, and a ruthenium-catalyzed Alder-ene reaction. Thus, the total synthesis of cis-solamin was achieved in 11 steps with an overall yield of 7.5%.
Göksel
Hülya
H
Institut für Chemie und Biochemie-Organische Chemie, Freie Universität Berlin, Takustrasse 3, 14195 Berlin, Germany.
Stark
Christian B W
CB
D029061:Annonaceae / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D017975:Ruthenium Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D005663:Furans; D017975:Ruthenium Compounds; C519987:cis-solamin; C027646:ruthenium tetraoxide