期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 76, 期 10, 页码 3909-3916出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo200337v
关键词
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资金
- National Institute of General Medical Sciences [NIH RO1 GM077309]
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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