Development of an enantiodivergent strategy for the total synthesis of (+)- and (-)-dragmacidin f from a single enantiomer of quinic Acid.
An enantiodivergent strategy for the total chemical synthesis of both (+)- and (-)-dragmacidin F beginning from a single enantiomer of quinic acid has been developed and successfully implemented. Although unique, the synthetic routes to these antipodes share a number of key features, including novel reductive isomerization reactions, Pd(II)-mediated oxidative carbocyclization reactions, halogen-selective Suzuki couplings, and high-yielding late-stage Neber rearrangements.
Garg
Neil K
NK
The Arnold and Mabel Beckman Laboratories of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Boulevard, MC 164-30, Pasadena, California 91125, USA.
Caspi
Daniel D
DD
Stoltz
Brian M
BM
D000818:Animals; D026121:Indole Alkaloids / Q000138:chemical synthesis*; D011161:Porifera / Q000737:chemistry; D011801:Quinic Acid / Q000737:chemistry*; D013237:Stereoisomerism
D026121:Indole Alkaloids; C492392:dragmacidin F; D011801:Quinic Acid