Reference no: EM133127440
Question 1. Explain the different outcomes of the following boron mediated enolate formation?
Question 2. Glucolipsin A, a glycolipid possessing glucokinase-activating properties, was discovered at Bristol-Myers Squibb, but the absolute stereochemistry of the natural product remined elusive. Fürstner and co-workers elucidated the absolute stereochemistry via synthesis and spectroscopic analysis of the natural macrolide and its C2-symmteric stereoisomers. In their approach, the utilized the Evans aldol reaction that provided the aldol product with good yield and excellent diastereo selectivity.
Fürstner, A. et al. J. Org. Chem. 2004, 69, 459-467.
Propose a method to synthesize the blue partin Glucolipsin A, using Evans's aldol reaction?Show reaction mechanism and explain the stereochemical outcome of the reaction.
Question 3. D. L. Boger et al. reported the total synthesis of Bleomycin A2. They devised an efficient synthesis for the construction of the tripeptide S, tetrapeptide S and pentapeptide S subunits of the natural product. In their strategy, they utilizedthe Evans aldol reactionwithN-Boc-D-alaninal that provided the aldol product with good yield and excellent diastereo selectivity.
Boger, D.L. et al. J. Org. Chem. 1992, 57, 4331-4333.
Propose a method to synthesize the blue partin Bleomycin A2 A, using Evans's aldol reaction? Show reaction mechanism and explain the stereochemical outcome of the reaction.
Attachment:- Glycolipid possessing.rar
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