EANTIOSELECTIVE TOTAL SYNTHESIS: (+)-IKARUGAMYCIN

  • Kurth, Mark J, (PI)
  • Kurth, Mark (PI)

Project: Research project

Project Details

Description

Herein is proposed an investigation of enantioselective C,C-bond formation
via the Claisen rearrangement. Both the broad synthetic applicability and
the intrinsic stereo-selectivity of this reorganization recommend its
development for use in enantioselective synthesis. Realization of this
goal will provide synthetic access to optically pure Alpha- and/or
Beta-substituted Gamma,Delta-unsaturated acids which will prove useful as
synthetic intermediates in the synthesis of chiral chemotherapeutics.
Developments of N-allylketene N,X-acetal Claisen substrates and Beta-alkoxy
allylic ester enolates which will undergo diastereoselective Claisen
rearrangement are proposed. These asymmetric procedures will be applied in
the enantioselective syntheses of the antibiotic agents (+)- ikarugamycin
(1) and (-)-botryodiplodin (2). Realization of these goals will provide
access to these natural compounds, interesting analogs, and generate new
chemistry of sufficient generality for future application in the synthesis
of other bioactive molecules. Specific aims of this proposed research are: i) to develop auxiliary reagent mediated diastereoselective aza-Claisen
rearrangement substrates applicable to enantioselective synthesis. ii) to develop diastereoselective Beta-alkoxy ester enolate Claisen
rearrangement substrates applicable to enantioselective synthesis. iii) to demonstrate the synthetic potential of these Claisen rearrangements
in a total synthesis of the antibiotic (-)-botryodiplodin (2). iv) to achieve a total synthesis of the naturally occurring antibiotic
(+)-ikarugamycin (1).
StatusFinished
Effective start/end date1/1/8512/31/87

Funding

  • National Institutes of Health
  • National Institutes of Health

ASJC

  • Medicine(all)
  • Immunology and Microbiology(all)

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