Phosphate Tether-Mediated Approach to the Formal Total Synthesis of (-)-Salicylihalamides A and B
Phosphate Tether-Mediated Approach to the Formal Total Synthesis of (-)-Salicylihalamides A and B
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DOI：
10.1021/jo200337v
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发表时间：
2011-05-20
影响因子：
3.6
通讯作者：
Hanson, Paul R.
中科院分区：
文献类型：
--
作者：
Chegondi, Rambabu;Tan, Mary M. L.;Hanson, Paul R.
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.
