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Total synthesis of (+)-lactacystin
1Department of Chemistry, Metcalf Center for Science and Engineering, Boston University, Boston, MA 02215, USA, Fax: (+1) 617-353-6466. panek@chem.bu.edu.
Angewandte Chemie (International Ed. in English)
|August 21, 2014
Summary
This study presents an efficient asymmetric synthesis of (+)-lactacystin, a neurotrophic compound. Key steps include a stereoselective crotylation and catalytic asymmetric aminohydroxylation for a crucial synthon.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Neuroscience
Background:
- (+)-Lactacystin is a neurotrophic metabolite from Streptomyces sp. OM-6519.
- Efficient asymmetric synthesis is crucial for obtaining biologically active compounds like lactacystin.
Purpose of the Study:
- To develop an efficient asymmetric synthesis of (+)-lactacystin.
- To utilize key stereoselective reactions for constructing the lactacystin molecule.
Main Methods:
- A double stereodifferentiating crotylation reaction between aldehyde and silane.
- Catalytic asymmetric aminohydroxylation for synthon preparation.
Main Results:
- The crotylation step achieved high diastereoselectivity (anti:syn >30:1).
- An efficient asymmetric synthesis of (+)-lactacystin was successfully established.
Conclusions:
- The developed synthetic route is efficient for producing (+)-lactacystin.
- Stereoselective crotylation and asymmetric aminohydroxylation are key enabling steps.