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. doi:10.7907/mref-rb43. https://resolver.caltech.edu/CaltechETD:etd-10312002-152412

Abstract

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 β-lactam 31 was accomplished via a 13-step sequence, which included several interesting intramolecular reactions.

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