Phosphate Tether-Mediated Approach to the Formal Total Synthesis of (-)-Salicylihalamides A and B
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Issue Date
2011-05-20Author
Chegondi, Rambabu
Tan, Mary M. L.
Hanson, Paul R.
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/jo200337v.
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Show full item recordAbstract
A concise formal synthesis of the cytotoxic macrolides (-)-salicylihalamides A and B is reported. Key features of the synthetic strategy include a chemoselective hydroboration, highly regio- and diastereoselective methyl cuprate addition, Pd-catalyzed formate reduction, and an E-selective ring-closing metathesis to construct the 12-membered macrocycle subunit. Overall, two routes have been developed from a readily prepared bicyclic phosphate (4-steps), a 13-step route and a more efficient 9-step sequence relying on regioselective esterification of a key diol.
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Citation
Chegondi, R., Tan, M. M. L., & Hanson, P. R. (2011). Phosphate Tether-Mediated Approach to the Formal Total Synthesis of (-)-Salicylihalamides A and B. The Journal of Organic Chemistry, 76(10), 3909–3916. http://doi.org/10.1021/jo200337v
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