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A modular phosphate tether-mediated divergent strategy to complex polyols
Hanson, Paul R. Jayasinghe, Susanthi Maitra, Soma Ndi, Cornelius N. Chegondi, Rambabu
Hanson, Paul R.
Jayasinghe, Susanthi
Maitra, Soma
Ndi, Cornelius N.
Chegondi, Rambabu
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Abstract
An efficient and divergent synthesis of polyol subunits utilizing a phosphate tether-mediated, one-pot, sequential RCM/CM/reduction process is reported. A modular, 3-component coupling strategy has been developed, in which, simple “order of addition” of a pair of olefinic-alcohol components to a pseudo-C 2-symmetric phosphoryl chloride, coupled with the RCM/CM/reduction protocol, yields five polyol fragments. Each of the product polyols bears a central 1,3-anti-diol subunit with differential olefinic geometries at the periphery.
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This investigation was generously supported by funds provided by the National Institute of General Medical Sciences (NIH R01 GM077309). The authors thank Dr. Justin Douglas and Sarah Neuenswander (KU) for assistance with NMR measurements and Dr. Todd Williams (KU) for HRMS analysis. The authors also thank the University of Kansas and the State of Kansas for support of our program. The authors also thank Materia, Inc. for supplying the metathesis catalyst.
Date
2014-10-07
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Beilstein-Institut
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Hanson_2014.pdf
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Phosphate Tether, One-pot, Sequential Processes, Organophosphorus, Polyol, Stereodivergent
Citation
Paul R Hanson, Susanthi Jayasinghe, Soma Maitra, Cornelius N Ndi, Rambabu Chegondi. "A modular phosphate tether-mediated divergent strategy to complex polyols." Beilstein J Org Chem. 2014; 10: 2332–2337. Published online 2014 October 7. http://dx.doi.org/10.3762/bjoc.10.242