# TOTAL SYNTHESIS OF THE ANTILEUKEMIC AGENT BRYOSTATIN 1

> **NIH NIH R01** · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · 1987 · $161,516

## Abstract

Although still largely untapped, the oceans have proven to be a source of
several families of marine natural products possessing potentially useful
pharmaceutical properties.  For instance, several compounds isolated from
Bugula neritina have shown promise in certain anticancer tests, and
bryostatin 1, a representative member of this group, indeed extends the
average lifetime of leukemic mice by 52-59%.  This project is specifically
aimed at the synthesis of bryostatin 1, C47H68O17, a 26-membered macrolide
with 11 chiral centers comprising a series of 1,2-and 1,3-diol moieties,
pyran rings, and olefinic linkages.  The compound is retrosynthetically
dissected into three major fragments, which will be assembled in the final
stages of the proposed synthesis.  Therefore, the entire scheme is highly
convergent thus rendering the actual execution of the synthesis practical,
despite the structural complexity of the target molecule.

All of the structural units embedded in bryostatin 1 can be constructed
through several methodologies developed recently in our or other
laboratories.  Stereochemical problems to be encountered during the course
of the synthesis will be resolved with the proper application of the
concept now termed multiple asymmetric induction.  The importance of this
concept in acyclic stereochemical control has now been fully recognized.
The pursuit of this project will undoubtedly enhance our synthetic
expertise and further help identify new fundamental problems yet to be
investigated in the field of organic synthesis.  Of primary benefit,
however, would be the wealth of information which could answer many
questions concerning the structure/activity relationship of bryostatin.  It
is definitely intended to submit adequate samples of this marine product
and its derivative for biological screenings.

## Key facts

- **NIH application ID:** 3175649
- **Project number:** 5R01CA037804-04
- **Recipient organization:** MASSACHUSETTS INSTITUTE OF TECHNOLOGY
- **SAM.gov UEI:** E2NYLCDML6V1
- **Principal Investigator:** SATORU MASAMUNE
- **Activity code:** R01 (R01, R21, SBIR, etc.)
- **Funding institute:** NIH
- **Fiscal year:** 1987
- **Award amount:** $161,516
- **Award type:** 5
- **Project period:** 1984-07-01 → 1988-05-31

## Primary source

NIH RePORTER: https://reporter.nih.gov/project-details/3175649

## Citation

> US National Institutes of Health, RePORTER application 3175649, TOTAL SYNTHESIS OF THE ANTILEUKEMIC AGENT BRYOSTATIN 1 (5R01CA037804-04). Retrieved via MORVS 2026-10-25 from https://api.morvs.ai/grant/nih/3175649. Licensed CC0.

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