# ACYCLIC STEREOSELECTION IN NATURAL PRODUCT SYNTHESIS

> **NIH NIH R01** · UNIVERSITY OF CALIFORNIA BERKELEY · 1987 · $181,155

## Abstract

The long-term objective of this project is development of effective methods
for control of relative and absolute stereochemistry in the synthesis of
conformationally-flexible, biologically-important molecules.  During the
first five years of the study attention was concentrated on a study of the
stereochemistry of the addition of preformed lithium enolates to aldehydes
(aldol additon reaction).  A number of useful reagents were developed and
applications in the total synthesis of macrolide antibiotics were
initiated.  In the coming grant period, it is intended to complete a total
synthesis of erythronolide A and carry out syntheses of methynolide and
tylonolide.  In addition, research on the application of stereoselective
aldol technology to the total synthesis of rare carbohydrates will
continue.  It is also planned to use methodology developed earlier in the
project for elucidation of the stereochemistry of the
biosynthetically-important archaebacterial lipids.  The possible utility of
the kinetic Michael addition of amide enolates to enones will be evaluated
as a method for realizing stereocontrol.  Four important carbon-carbon
bond-forming reactions involving organosilicon compounds will be
systematically investigated from a stereochemical standpoint.  Finally, the
use of chiral auxillaries for achieving absolute asymmetric induction in
the addition of metal enolates to aldehydes and ketones will be studied.

## Key facts

- **NIH application ID:** 3125985
- **Project number:** 5R01AI015027-10
- **Recipient organization:** UNIVERSITY OF CALIFORNIA BERKELEY
- **SAM.gov UEI:** GS3YEVSS12N6
- **Principal Investigator:** CLAYTON H HEATHCOCK
- **Activity code:** R01 (R01, R21, SBIR, etc.)
- **Funding institute:** NIH
- **Fiscal year:** 1987
- **Award amount:** $181,155
- **Award type:** 5
- **Project period:** 1978-09-01 → 1988-08-31

## Primary source

NIH RePORTER: https://reporter.nih.gov/project-details/3125985

## Citation

> US National Institutes of Health, RePORTER application 3125985, ACYCLIC STEREOSELECTION IN NATURAL PRODUCT SYNTHESIS (5R01AI015027-10). Retrieved via MORVS 2026-10-25 from https://api.morvs.ai/grant/nih/3125985. Licensed CC0.

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