An approach to the total synthesis of (?)-naphthyridinomycin A

Citation

Biller, Scott Adams (1982) An approach to the total synthesis of (?)-naphthyridinomycin A. Dissertation (Ph.D.), California Institute of Technology. http://resolver.caltech.edu/CaltechETD:etd-10312002-152412

Abstract

NOTE: Text or symbols not renderable in plain ASCII are indicated by [...]. Abstract is included in .pdf document. An approach to the total synthesis of the quinone antibiotic (?)-naphthyridinomycin A is described. This research has thus far culminated in the preparation of the advanced, pentacyclic intermediate _93_. The structure of phenol _93_ was secured by an X-ray crystallographic study of its benzoate ester. Intermediate _93_ was constructed from tricyclic lactam _21_, phenol _19a_ and methyl glyoxalate, employing a stereoselective amidoalkylation reaction and an intramolecular Friedel-Crafts alkylation as key [...] transformations. With regard to the amidoalkylation step, several new methods for the generation of acylimmonium ions were developed in the course of model studies. The synthesis of tricyclic lactam _21_ from the readily available bicyclic [beta]-lactam _31_ was accomplished via a 13-step sequence, which included several interesting intramolecular reactions.

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