期刊
ORGANIC LETTERS
卷 16, 期 6, 页码 1646-1649出版社
AMER CHEMICAL SOC
DOI: 10.1021/ol5002973
关键词
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资金
- Ministry of Education, Culture, Sports, Science and Technology (MEXT) of Japan [12045232, 24105530]
- Grants-in-Aid for Scientific Research [26102736, 25560399, 25108705, 26460007, 23390007, 24105530] Funding Source: KAKEN
Total synthesis of SB-203207 (1) was achieved, beginning with a desymmetrical C-H insertion reaction of a diazoester bearing our recently developed chiral auxiliary. Utilizing the optically active bicyclo[3.3.0]octane ring, four stereogenic centers were efficiently constructed in sequence. Finally, mild oxidation of 27 to carboxylic acid via a cyanohydrin intermediate and hydrolysis of cyanide to carboxyamide in the presence of the labile enamide group completed an efficient total synthesis of 1.
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