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|All Authors / Contributors:||
Guillaume Bernadat; Jieping Zhu; Université de Paris-Sud. Faculté des Sciences d'Orsay (Essonne).
|Description:||1 vol. (238 p.) : ill. ; 21 cm.|
|Responsibility:||Guillaume Bernadat ; [sous la direction de] Jieping Zhu.|
Lemonomycin is a member of the tetrahydroisoquinolin antitumor antibiotics family. Its structure features a highly substituted tetrahydroisoquinolin, as well as a diazabicyclo[3.2.1]octane system. An aminosugar moiety is also present in the structure. After a short review of existing synthetic works towards lemonomycin and structurally related molecules, several synthetic routes towards this natural product are envisioned and their implementation is disclosed. A method to prepare the pyrrolidine ring through an allylsilane amidoalkylation reaction is first presented. This method is then applied in different strategies towards lemonomycin. Some routes begin with the formation of the tetrahydroisoquinoline ring system by a Pictet-Spengler reaction. Different types of internal nucleophiles are then tested in order to build the bridged bicyclic system. In other routes, the diazabicyclo[3.2.1]octane core is built first. Several strategies are then tried in order to couple the aromatic moiety required for the tetrahydroisoquinoline: phenolic type Mannich reaction, phenolic type aldol reaction, benzyle bromide N-alkylation. Eventually, a stereocontrolled synthesis of the 2,6-dideoxy-4-amino sugar from D-threonine is presented.