# TOTAL SYNTHESIS OF ACTINOBOLIN AND BACTOBOLIN

> **NIH NIH R01** · BRANDEIS UNIVERSITY · 1987 · $100,990

## Abstract

This proposal describes an efficient approach to the synthesis of the
antitumor antibiotics actinobolin and bactobolin.  Bactobolin in
particular, is a promising antitumor agent.  Our route for the synthesis of
actinobolin is based on an analysis of the likely biogenetic pathway.  An
acyclic pentaketide precursor will be cyclized to a cyclohexanone
carboxylate using either a mercury mediated or an epoxide mediate
approach.  The Delta-lactone will be formed by halolactonization, a
procedure which will allow the introduction of the amino group.  In the
optimal case only nine steps will be needed to synthesize actinobolin.

The syntheses of actinobolin and bactobolin have been designed to allow the
synthesis of analogs.  These analogs will be useful in developing
structure-activity relationships and may also prove to be more useful
pharmacological agents.  These syntheses are efficient and
stereoselective.  This proposal should lead to the development of new
synthetic methods and a better understanding of the chemistry of
actinobolin and bactobolin.

In the course of model studies, it has been found that bromolactonization
of Gamma,Delta-unsaturated acids gives predominantly the Delta-lactone
while iolodactonization gives predominantly the Gamma-lactone.  The scope
of this reaction will be explored with a variety of substrates to determine
the extent of these differences in regio- and stereoselectivity.  In the
course of elaborating the scope of bromolactonization as a route to
Delta-lactones, a variety of naturally occurring dideoxy sugars will be
synthesized.

## Key facts

- **NIH application ID:** 3178184
- **Project number:** 5R01CA039336-03
- **Recipient organization:** BRANDEIS UNIVERSITY
- **SAM.gov UEI:** MXLZGAMFEKN5
- **Principal Investigator:** BARRY B. SNIDER
- **Activity code:** R01 (R01, R21, SBIR, etc.)
- **Funding institute:** NIH
- **Fiscal year:** 1987
- **Award amount:** $100,990
- **Award type:** 5
- **Project period:** 1985-09-05 → 1988-08-31

## Primary source

NIH RePORTER: https://reporter.nih.gov/project-details/3178184

## Citation

> US National Institutes of Health, RePORTER application 3178184, TOTAL SYNTHESIS OF ACTINOBOLIN AND BACTOBOLIN (5R01CA039336-03). Retrieved via MORVS 2026-10-25 from https://api.morvs.ai/grant/nih/3178184. Licensed CC0.

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