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Phosphate Tether-Mediated Approach to the Formal Total Synthesis of (-)-Salicylihalamides A and B
Chegondi, Rambabu Tan, Mary M. L. Hanson, Paul R.
Chegondi, Rambabu
Tan, Mary M. L.
Hanson, Paul R.
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Abstract
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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2011-05-20
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American Chemical Society
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Hanson_2011.pdf
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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