Published April 27, 2005
| Version Supplemental Material
Journal Article
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Development of an Enantiodivergent Strategy for the Total Synthesis of (+)- and (−)-Dragmacidin F from a Single Enantiomer of Quinic Acid
Abstract
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.Attached Files
Supplemental Material - ja050586vsi20050220_081818.pdf
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ja050586vsi20050220_081818.pdf
Additional details
Identifiers
- Eprint ID
- 74461
- DOI
- 10.1021/ja050586v
- Resolver ID
- CaltechAUTHORS:20170222-093427303
Related works
- Describes
- http://pubs.acs.org/doi/suppl/10.1021/ja050586v (URL)
Funding
- NIH
- R01GM65961-01
- National Defense Science and Engineering Graduate (NDSEG) Fellowship
- Eli Lilly
- AstraZeneca
- Boehringer-Ingelheim
- Johnson and Johnson
- Pfizer
- Merck
- Amgen
- Research Corporation
- Roche
- GlaxoSmithKline
Dates
- Created
-
2017-02-22Created from EPrint's datestamp field
- Updated
-
2021-11-11Created from EPrint's last_modified field