A kind of asymmetric synthesis method of chiral benzofuran spiro indole oxide compounds

Abstract

The invention provides an asymmetric synthesis method of a chiral benzofuran spiro indole compound represented by formula (I), and the synthesis method is carried out according to the following steps: The nitroalkene compound is mixed with the oxidized indole compound represented by the formula (III), a chiral hydrogen bond catalyst, and an organic solvent, and the reaction is carried out at ‑40~60° C. for 1~240h to obtain the compound represented by the formula (IV), Add iodine source additive and oxidant to the compound represented by formula (IV), react at -40~60°C for 1~48h, the reaction solution is post-treated to obtain the chiral benzofuran spiro indole represented by formula (I) compound; the reaction conditions of the present invention are mild, the product yield is high, and the selectivity is excellent.

Description

[0001] (1) Technical field

[0002] The invention relates to an asymmetric synthesis method of chiral benzofuran spirooxindole compounds.

[0003] (2) Background technology

[0004] Chiral spirooxindole compounds exist in a large number of biologically active natural products and clinical medicines, which have a wide range of biological activities. Indole, pyrazoline spirooxindole, isoxazoline spirooxindole, etc., such as: Compound A, a Chinese herbal medicine alkaloid named (-)-Horsfiline, exists in Phoebe genus Schima, mainly used In terms of pain relief and sedation; Tan et al. reported that Compound B has a good inhibitory effect on the growth of human breast cancer cells. Further mechanistic studies have found that Compound B mainly inhibits the step-by-step phosphorylation in the signaling pathway of mitogen-activated protein kinase. Proliferation of human cancer cell lines (acute leukemia T cell line, human breast cancer cell line and HeLa cell line) by the antitoxin of...

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