# ORGANOTRANSITION METAL ENTRY TO ANTITUMOR QUINONES

> **NIH NIH R01** · EMORY UNIVERSITY · 1990 · $180,998

## Abstract

The development of general, broadly applicable methods for
antitumor quinone synthesis is proposed.  Emphasis is placed on the
use of organotransition metal chemistry in the development of the
synthetic methods, because of the unique ability of transition
metal species to facilitate the formation of carbon-carbon bonds
under very mild conditions in the presence of sensitive organic
functional groups, and because of the ability of transition metal
species to stabilize reactive organic intermediates of use in
synthetic transformations.  A variety of objectives are met by this
goal.  Simple methods of quinone synthesis that allow flexible
variation of the substitutents on the quinone core will facilitate
the rapid study of structure-activity relationships of antitumor
quinones.  The chemistry developed throughout this proposal will
also enable the synthesis of complex quinone based natural products
to be tackled, and in so doing provide quantities of material
needed for detailed biological assay.  In a more general sense, the
proposed chemistry provides a framework upon which new organic and
organometallic reactions can be developed.

For the forthcoming grant period, effort will be made in three
distinct areas; organometallic development, organic development,
and total synthesis.  Development of the organometallic aspects of
the project will focus on studies of metallacycles as precursors
to quinones, phenols, and anilines, and the preparation and
reactions of metal pi complexes of quinones quinols, and 6-
oxohexadienyls (prepared by O-alkylation of quinone complexes) will
be studied.  Within the organic realm we will continue to develop
very simple synthetic routes to cyclobutenediones and
benzocylobutenediones.  The cyclobutenedione chemistry has to led
to simple thermal route to highly substituted quinones that
presumable proceeds through vinylketene intermediates.  The use of
cyclobutenedione derivatives in the syntheses of phenols, anilines,
and pyridones will be explored.  Highly functionalized quinones
should be useful for the synthesis of other types of complex
molecules.  Using traditional methods of synthesis, properly
substituted quinones as starting materials for the preparation of
other important compounds would be too difficult to prepare.
However, many appropriately functionalized quinones are easily
prepared from alkynes and maleoylcobalt complexes, so quinones
synthesized via the chemistry developed in this proposal could
become valuable precursors to other classes of compounds such as
indoles.

The total synthesis goals will center on completing the current
approaches to the antitumor antibiotic royleanone and saframycin
B.  Other total synthesis goals will be chosen to (a) allow the
preparation of substances for biological assay and to (b) provide
a framework upon which we can continue to probe the development of
our various routes to quinone based molecules.  New and interesting
organic and organometallic compounds will be sent ...

## Key facts

- **NIH application ID:** 3179722
- **Project number:** 5R01CA040157-07
- **Recipient organization:** EMORY UNIVERSITY
- **SAM.gov UEI:** S352L5PJLMP8
- **Principal Investigator:** LANNY S LIEBESKIND
- **Activity code:** R01 (R01, R21, SBIR, etc.)
- **Funding institute:** NIH
- **Fiscal year:** 1990
- **Award amount:** $180,998
- **Award type:** 5
- **Project period:** 1979-07-01 → 1993-04-30

## Primary source

NIH RePORTER: https://reporter.nih.gov/project-details/3179722

## Citation

> US National Institutes of Health, RePORTER application 3179722, ORGANOTRANSITION METAL ENTRY TO ANTITUMOR QUINONES (5R01CA040157-07). Retrieved via MORVS 2026-10-25 from https://api.morvs.ai/grant/nih/3179722. Licensed CC0.

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