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Development of an Enantiodivergent Strategy for the Total Synthesis of (+)- and (−)-Dragmacidin F from a Single Enantiomer of Quinic Acid

Garg, Neil K. and Caspi, Daniel D. and Stoltz, Brian M. (2005) Development of an Enantiodivergent Strategy for the Total Synthesis of (+)- and (−)-Dragmacidin F from a Single Enantiomer of Quinic Acid. Journal of the American Chemical Society, 127 (16). pp. 5970-5978. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20170222-093427303

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja050586vDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja050586vPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja050586vRelated ItemSupporting Information
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
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.
Funders:
Funding AgencyGrant Number
NIHR01GM65961-01
National Defense Science and Engineering Graduate (NDSEG) FellowshipUNSPECIFIED
Eli LillyUNSPECIFIED
AstraZenecaUNSPECIFIED
Boehringer-IngelheimUNSPECIFIED
Johnson and JohnsonUNSPECIFIED
PfizerUNSPECIFIED
MerckUNSPECIFIED
AmgenUNSPECIFIED
Research CorporationUNSPECIFIED
RocheUNSPECIFIED
GlaxoSmithKlineUNSPECIFIED
Issue or Number:16
Record Number:CaltechAUTHORS:20170222-093427303
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170222-093427303
Official Citation:Development of an Enantiodivergent Strategy for the Total Synthesis of (+)- and (−)-Dragmacidin F from a Single Enantiomer of Quinic Acid Neil K. Garg, Daniel D. Caspi, and Brian M. Stoltz Journal of the American Chemical Society 2005 127 (16), 5970-5978 DOI: 10.1021/ja050586v
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:74461
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:22 Feb 2017 19:29
Last Modified:03 Oct 2019 16:39

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