期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 9, 期 7, 页码 2512-2517出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c0ob01115k
关键词
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资金
- National Natural Science Foundation of China [20802005, 20972007]
- National Basic Research Program of China (973 Program) [2010CB833200]
- NCET
- Peking University
The total synthesis of protein kinase C activator (-)-indolactam V (IL-V) has been successfully completed with two separate approaches: From known 4-nitrotryptophan derivative 3 in 8 steps (49% overall yield) and from L-glutamic acid in 12 steps (18% overall yield), where 4-nitrotryptophanol derivative 4 served as a key intermediate. Derivatives 3 and 4, both incorporating indole 4-substitution and the C-9 stereocenter in IL-V, were synthesized via the Pd-catalyzed indole synthesis from 3-nitro-2-iodoaniline 5 with aldehydes 6 and 7, respectively. Aldehyde 7 was, meanwhile, synthesized from L-glutamic acid in 5 steps (68% yield). Lactamization of the 9-membered ring was achieved using HATU in THF in good yield.
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