Direct coupling of indoles with carbonyl compounds: short, enantioselective, gram-scale synthetic entry into the hapalindole and fischerindole alkaloid families.
The invention of a method for the direct union of indoles and carbonyl compounds (ketones, amides, esters) is described. Using this new method, a short, enantioselective, gram-scale and protecting group-free synthetic entry to the fischerindole and hapalindole indole alkaloid family has been achieved from carvone and indole. Total syntheses of (+)-hapalindole Q and (-)-12-epi-fischerindole U isothiocyanate are reported. The absolute stereochemistry of the latter natural product has also been determined.
Baran
Phil S
PS
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA. pbaran@scripps.edu
Richter
Jeremy M
JM
D000447:Aldehydes / Q000737:chemistry*; D000470:Alkaloids / Q000138:chemical synthesis*; D000081005:Cyclohexane Monoterpenes; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D039821:Monoterpenes; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry
D000447:Aldehydes; D000470:Alkaloids; D000081005:Cyclohexane Monoterpenes; D007211:Indoles; D039821:Monoterpenes; D013729:Terpenes; C491991:fischerindole; C438931:hapalindole Q; C006923:carvone; C030374:indole