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Total Synthesis of Dolabelide C: A Phosphate-Mediated Approach
Hanson, Paul R. Chegondi, Rambabu Nguyen, John Thomas, Christopher Daniel Waetzig, Joshua David Whitehead, Alan
Hanson, Paul R.
Chegondi, Rambabu
Nguyen, John
Thomas, Christopher Daniel
Waetzig, Joshua David
Whitehead, Alan
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Abstract
The first synthesis of dolabelide C (1), a cytotoxic marine macrolide, is reported utilizing a phosphate tether-mediated approach. Bicyclic phosphates (S,S,SP)-5 and (R,R,RP)-5 serve as the central building blocks for the construction of two major 1,3-anti-diol subunits in 1 through selective cleavage pathways, regioselective olefin reduction and cross-metathesis. Overall, phosphate-mediated processes provided copious amounts of both major subunits allowing for a detailed RCM macrocyclization study to the 24-membered macrolactone 1.
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2011-06-03
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American Chemical Society
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Hanson, P. R., Chegondi, R., Nguyen, J., Thomas, C. D., Waetzig, J. D., & Whitehead, A. (2011). Total Synthesis of Dolabelide C: A Phosphate-Mediated Approach. The Journal of Organic Chemistry, 76(11), 4358–4370. http://doi.org/10.1021/jo2003506