Studies towards the total synthesis of bryostatin 3
Abstract/Contents
- Abstract
- The bryostatins, first isolated by Petit et al. from the marine bryozoan Bugula neritina, are a family of 21 macrolides with potent antineoplastic, immunopotentiating, synaptogenesis-inducing and latent HIV-modulating activity. Beneficial effects as a post-stroke treatment and for restoring the blood brain barrier after traumatic blast injuries have also been reported. While the exact mechanism of action remains an ongoing area of research, it has become clear that bryostatins act as agonists of protein kinase C with low nanomolar affinities for their target. Within the bryostatins bryostatin 3 stands out as the most complex member of this family of natural products. While the majority of bryostatins share a common macrocyclic backbone with three tetrahydropyran rings bryostatin 3 features an additional butenolide ring fused to the C-ring. Our retrosynthetic plan for bryostatin 3 disconnects the target into three fragments of similar complexity and we were able to elaborate these fragments to a protected version of bryostatin 3. This direct precursor to the natural product was synthesized in 22 steps (longest linear, 31 total). The only previous total synthesis of bryostatin 3 was accomplished in 43 steps (longest linear, 89 total).
Description
| Type of resource | text |
|---|---|
| Form | electronic; electronic resource; remote |
| Extent | 1 online resource. |
| Publication date | 2016 |
| Issuance | monographic |
| Language | English |
Creators/Contributors
| Associated with | Buckl, Andreas Korbinian |
|---|---|
| Associated with | Stanford University, Department of Chemistry. |
| Primary advisor | Trost, Barry M |
| Thesis advisor | Trost, Barry M |
| Thesis advisor | Kool, Eric T |
| Thesis advisor | Wender, Paul A |
| Advisor | Kool, Eric T |
| Advisor | Wender, Paul A |
Subjects
| Genre | Theses |
|---|
Bibliographic information
| Statement of responsibility | Andreas Korbinian Buckl. |
|---|---|
| Note | Submitted to the Department of Chemistry. |
| Thesis | Thesis (Ph.D.)--Stanford University, 2016. |
| Location | electronic resource |
Access conditions
- Copyright
- © 2016 by Andreas Korbinian Buckl
- License
- This work is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported license (CC BY-NC).
Also listed in
Loading usage metrics...