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An Approach to the Total Synthesis of (±)-Naphthyridinomycin A


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.


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.

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:Public (worldwide access)
Research Advisor(s):
  • Bercaw, John E.
Thesis Committee:
  • Bercaw, John E. (chair)
  • Evans, David A.
  • Grubbs, Robert H.
  • Dervan, Peter B.
Defense Date:4 December 1981
Funding AgencyGrant Number
Earle C. Anthony FellowshipUNSPECIFIED
Record Number:CaltechETD:etd-10312002-152412
Persistent URL:
Default Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:4337
Deposited By: Imported from ETD-db
Deposited On:01 Nov 2002
Last Modified:16 Apr 2021 23:17

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