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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.

Item Type:Thesis (Dissertation (Ph.D.))
Subject Keywords:antibiotics; quinone
Degree Grantor:California Institute of Technology
Division:Chemistry and Chemical Engineering
Major Option:Chemistry
Awards:The Herbert Newby McCoy Award, 1981
Thesis Availability:Restricted to Caltech community only
Research Advisor(s):
  • Evans, David A.
Thesis Committee:
  • Unknown, Unknown
Defense Date:4 December 1981
Record Number:CaltechETD:etd-10312002-152412
Persistent URL:http://resolver.caltech.edu/CaltechETD:etd-10312002-152412
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:4337
Collection:CaltechTHESIS
Deposited By: Imported from ETD-db
Deposited On:01 Nov 2002
Last Modified:26 Dec 2012 03:07

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