# NATURAL PRODUCT SYNTHESIS VIA ELECTRON DEFICIENT IMINES

> **NIH NIH R01** · PENNSYLVANIA STATE UNIVERSITY, THE · 1993 · $186,393

## Abstract

The primary goal of this research project is to develop and exploit
pericyclic and related reactions of electron deficient imines and
iminium compounds within the general context of natural product
synthesis.  It is likely that useful new synthetic methodology
applicable to the preparation of nitrogen heterocycles and other
nitrogen-containing compounds will involve from these studies.
This methodology should prove valuable to synthetic chemists in the
pharmaceutical industry and others working in health-related
fields.

ln particular, we plan to develop short and efficient chiral total
syntheses of the potent antitumor compounds narciclasine and
neplanocin A using this methodology.  Narciclasine is a member of
the Amaryllidaceae alkaloid group.  This compound and its analogs
show significant cytostatic activity.  Neplanocin A is a nucleoside
analog which has a carbocyclic ring in place of ribose.  It and its
congeners, such as aristeromycin, have strong antitumor and
antiviral properties.

In addition, we will further explore the scope of our methodology
by its application to a diverse and challenging group of
heterocyclic structures.  Included are the unusual antifungal
alkaloids papuamine and/or haliclonadiamine produced by a marine
sponge.  Other targets include the Ergot alkaloids lysergic acid
and paspiclavine which we hope to prepare by short,
stereocontrolled routes.  Another target which will test our
methodology is the morphinan structure.  This molecule will be
prepared in a chiral synthesis from mandelic acid.  Hopefully the
approach can eventually be applied to more complex morphine
alkaloids.  lt is our intention to improve upon existing syntheses
in the above cases in terms of both efficiency and
stereoselectivity.

## Key facts

- **NIH application ID:** 3172026
- **Project number:** 5R01CA034303-11
- **Recipient organization:** PENNSYLVANIA STATE UNIVERSITY, THE
- **SAM.gov UEI:** NPM2J7MSCF61
- **Principal Investigator:** STEVEN M. WEINREB
- **Activity code:** R01 (R01, R21, SBIR, etc.)
- **Funding institute:** NIH
- **Fiscal year:** 1993
- **Award amount:** $186,393
- **Award type:** 5
- **Project period:** 1983-06-01 → 1994-06-30

## Primary source

NIH RePORTER: https://reporter.nih.gov/project-details/3172026

## Citation

> US National Institutes of Health, RePORTER application 3172026, NATURAL PRODUCT SYNTHESIS VIA ELECTRON DEFICIENT IMINES (5R01CA034303-11). Retrieved via MORVS 2026-10-25 from https://api.morvs.ai/grant/nih/3172026. Licensed CC0.

---

*[NIH grants dataset](/datasets/nih-grants) · CC0 1.0*