Total Synthesis of Dolabelide C: A Phosphate-Mediated Approach

Hanson, Paul R.; Chegondi, Rambabu; Nguyen, John; Thomas, Christopher D.; Waetzig, Joshua D.; Whitehead, Alan

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Issue Date

2011-06-03

Author

Hanson, Paul R.

Chegondi, Rambabu

Nguyen, John

Thomas, Christopher D.

Waetzig, Joshua D.

Whitehead, Alan

Publisher

American Chemical Society

Type

Article

Article Version

Scholarly/refereed, author accepted manuscript

Rights

This document is the Accepted Manuscript version of a Published Work that appeared in final form in the Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/jo2003506.

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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.

Citation

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

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