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Published April 27, 2005 | Supplemental Material
Journal Article Open

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.

Additional Information

© 2005 American Chemical Society. Received 28 January 2005. Published online 2 April 2005. Published in print 1 April 2005. The authors thank the NIH-NIGMS (Grant R01 GM65961-01), the NDSEG (predoctoral fellowship to N.K.G.), Eli Lilly (predoctoral fellowship to D.D.C.), AstraZeneca, Boehringer Ingelheim, Johnson & Johnson, Pfizer, Merck, Amgen, Research Corp., Roche, and GlaxoSmithKline for generous funding. Drs. R. Riccio and A. Casapullo are acknowledged for an authentic sample of (−)-dragmacidin F. We also thank the Dervan and MacMillan laboratories for helpful discussions and the use of instrumentation.

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Supplemental Material - ja050586vsi20050220_081818.pdf


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