Stereoselective syntheses of the 2-Isopropenyl-2,3-dihydrobenzofuran nucleus: potential chiral building blocks for the syntheses of tremetone, hydroxytremetone, and rotenone.
The first enantioselective synthesis of the 2-isopropenyl-2,3-dihydrobenzofuran skeleton of tremetone and hydroxytremetone from (E)-4-(2-hydroxyphenyl)-2-methyl-2-butenyl methyl carbonate and (E)-4-(2,6-dihydroxyphenyl)-2-methyl-2-butenyl methyl carbonate, respectively, is described. The key step is a catalytic palladium-mediated reaction in the presence of the chiral Trost ligand.
Pelly
Stephen C
SC
Molecular Sciences Institute, School of Chemistry, University of the Witwatersrand, PO Wits 2050, Johannesburg, South Africa.
Govender
Sameshnee
S
Fernandes
Manuel A
MA
Schmalz
Hans-Günther
HG
de Koning
Charles B
CB
D001572:Benzofurans / Q000737:chemistry*; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry*; D012402:Rotenone / Q000737:chemistry*; D013237:Stereoisomerism; D014223:Triamterene / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D001572:Benzofurans; D010936:Plant Extracts; C009519:tremetol; D012402:Rotenone; C026475:hydroxytriamterene sulfate ester; C105430:benzofuran; D014223:Triamterene