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Total synthesis of bryostatin 3
Barry M Trost1, Youliang Wang2, Andreas K Buckl2
1Department of Chemistry, Stanford University, Stanford, CA 94305-5080, USA. bmtrost@stanford.edu.
Science (New York, N.Y.)
|May 30, 2020
Summary
Researchers achieved a concise total synthesis of bryostatin 3, a complex marine natural product. This new method significantly reduces the number of steps required for its synthesis, making it more accessible.
Area of Science:
- Marine Natural Products Chemistry
- Organic Synthesis
- Medicinal Chemistry
Background:
- Bryostatins are a class of 21 complex marine natural products known for potent biological activities.
- Bryostatin 3 is the most structurally complex among the bryostatin family.
- Previous total syntheses of bryostatin 3 were lengthy, with one requiring 43 linear steps and 88 total steps.
Purpose of the Study:
- To develop a concise and efficient total synthesis of bryostatin 3.
- To overcome the synthetic challenges posed by the structural complexity of bryostatin 3.
- To establish a more accessible route to this important marine natural product.
Main Methods:
- Employed a highly convergent synthetic strategy.
- Utilized highly atom-economical and chemoselective chemical transformations.
- Leveraged the unique reactivity of alkynes to reduce the overall step count.
Main Results:
- Achieved a total synthesis of bryostatin 3 in 22 steps (longest linear sequence) and 31 total steps.
- The synthetic plan was significantly more concise than previous efforts.
- Demonstrated the utility of alkyne-based chemistry in streamlining complex molecule synthesis.
Conclusions:
- A highly efficient and convergent total synthesis of bryostatin 3 has been successfully developed.
- This streamlined approach significantly reduces the synthetic burden, making bryostatin 3 more accessible for further research.
- The strategy highlights the power of modern synthetic methodologies in tackling complex natural products.
