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Total Synthesis of Bryostatin 2
Abstract
The total synthesis of the marine macrolide bryostatin 2 is described. The synthesis plan relies on aldol and directed reduction steps in order to construct the anti -1,3-diol array present in each of the principal subunits (A, B, and C). These fragments were coupled using a Julia olefination and subsequent sulfone alkylation. A series of functionalization reactions provided a bryopyran seco acid, which was macrolactonized under Yamaguchi conditions. Installation of the two enoate moieties took advantage of asymmetric phosphonate and aldol condensation strategies. Reduction of the C 20 ketone and simple protecting group operations then completed the synthesis of bryostatin 2. This flexible approach should provide access to a series of new analogues of this clinically important marine natural product.
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Citations
Cited by
Impact of Natural Products on Developing New Anti-Cancer Agents
Cragg, G. M., Grothaus, P. G., & Newman, D. J. (2009) · Chemical Reviews · doi:10.1021/cr900019j · Cited by 1,302
Function-Oriented Synthesis, Step Economy, and Drug Design
Wender, P. A., Verma, V. A., Paxton, T. J., & Pillow, T. H. (2008) · Accounts of Chemical Research · doi:10.1021/ar700155p · Cited by 1,204
Drugs from the deep: Marine natural products as drug candidates
Haefner, B. (2003) · Drug Discovery Today · doi:10.1016/s1359-6446(03)02713-2 · Cited by 740
Search and Discovery Strategies for Biotechnology: the Paradigm Shift
Bull, A. T., Ward, A. C., & Goodfellow, M. (2000) · Microbiology and Molecular Biology Reviews · doi:10.1128/mmbr.64.3.573-606.2000 · Cited by 477
Natural Products as a Foundation for Drug Discovery
Beutler, J. A. (2009) · Current Protocols in Pharmacology · doi:10.1002/0471141755.ph0911s46 · Cited by 296
Metadata
- Authors
- Evans, D. A., Carter, P. H., Carreira, E. M., Charette, A. B., Prunet, J. A., & Lautens, M.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 1999-08-01
- Volume
- 121
- Issue
- 33
- Pages
- 7540-7552
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2950215543
- Cited by
- 254
- References
- 0
- FWCI
- 7.98
- Type
- journal article
- Language
- en
- Open access
- closed
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