Preparation method of sulfur-containing marine natural product Sunshiinamide

Through the new synthesis route, the synthesis process of Sunshinamide is simplified, the complexity of macrolide and intermediate protection operations in the existing methods is solved, the synthesis efficiency is improved, and the synthesis of analogs is facilitated, which is promoted. Structural-activity relationship and biological research.

CN119462824APending Publication Date: 2025-02-18FUDAN UNIVERSITY
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Patent Information

Application Number
CN202310999767.9
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2023-08-09
Publication Date
2025-02-18

AI Technical Summary

Technical Problem

The existing full synthesis method of Sunshinamide has macrolithiatic reactions that need to be carried out at extremely dilute concentrations, resulting in a decrease in the molecular weight of the product; the key intermediate 7a requires cumbersome hydroxyl protection and dechirective auxiliary operations; and the diversity of synthesis of Sunshinamide analogs inconvenient.

Method used

A new synthetic route is adopted, in which chiral compound 5a does not require hydroxyl protection and dechirectal auxiliaries, but is directly used to perform ammonia-removal reactions with amino acid fragments; the ring is constructed by macrolide rather than macrolide Lipopeptide; construct disulfide bonds in the molecule before macrocyclization to form an 8-membered ring intermediate, reducing the Trt protecting group, thereby reducing the molecular weight of the macrocyclization precursor.

Benefits of technology

It improves the synthesis efficiency of Sunshinamide, simplifies the synthesis process, facilitates the diversity synthesis of Sunshinamide analogs, and is conducive to its structure-activity relationship and biological research.

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Abstract

The invention belongs to the technical field of chemical synthesis, and particularly relates to a novel preparation method of a sulfur-containing marine natural product Sunshiinamide. A series of Sunshiinamide analogues can be conveniently synthesized on the basis of a large number of experiments and by adjusting reagents used in related reactions, and compared with an existing method, the method has the remarkable difference that a chiral compound 5a does not need hydroxyl protection and chiral prosthetic group removal operation and then is linked with an amino acid fragment through subsequent condensation reaction, and the chiral compound 5a can be used for preparing the Sunshiinamide analogues. But can be directly used for ammonolysis reaction with amino acid fragments; the macrocyclization of the cyclic lipopeptide is not prepared through macrocyclic lactamization, but is prepared through macrocyclic lactonization; before the macrocyclization reaction of the key cyclic lipopeptide, an intramolecular disulfide bond is firstly constructed, an 8-membered ring intermediate is formed, and two Trt protecting groups are removed, so that the molecular weight of a macrocyclization precursor is reduced, and the molecular weight of a key macrocyclization product is not obviously reduced, thereby being beneficial to improving the efficiency. The invention is beneficial to the structure-function relationship or related biological research of the series of Sunshiinamide analogues.
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