期刊
ORGANIC LETTERS
卷 21, 期 17, 页码 6603-6607出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b02015
关键词
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资金
- National Natural Science Foundation of China [21572085, 21272098, 21572086]
- Program for Changjiang Scholars and Innovative Research Team in University [PCSIRT: IRT_15R28]
- Fundamental Research Funds for the Central Universities [FRFCU: lzujbky-2016-ct02]
- 111 Project of MOE [111-2-17]
Starting from the commercially available 4-bromoindole, a concise and efficient enantioselective formal synthesis of (+)-cycloclavine (1) in 13 steps with 2.0% overall yield and a total synthesis of (+)-5-epi-cycloclavine (2) in 14 steps with 3.3% overall yield were achieved. Key features of the syntheses include the addition of a Grignard reagent to the C=N/Heck reaction sequence to construct the fused 6-5-6 ring systems, cyclopropanation, an ester aminolysis reaction, and the first example of the construction of a 3-azabicyclo[3,1,0]hexane through an intramolecular [3 + 2] cycloaddition/nitrogen extrusion.
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