maday - chemistry · 2020. 1. 29. · title: maday.pptx author: william wulff created date:...
Post on 20-Sep-2020
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Synthesis of Vallesamidine PresentedbyMitchellMaday
Background
• MonoterpeneindolealkaloidisolatedfromVallesiadichotoma
• Onlyracemicproductbeensynthesizedbefore
Goal
Forming the Nitro alkene
1,4 addi>on of Diethylmalonate
Lactamiza>on
Krapcho Decarboxyla>on
Allyla>on
Reduc>on of Nitro group
Cu and amino acid catalyzed coupling
Carbamate forma>on
2 Different Reduc>on pathways
Pathway A: create a thioamide
Thiolacam reduc>on
Aldehyde genera>on
Protec>ng the amine
Reduc>on pathway B
Protec>ng the Aldehyde
Amide reduc>on
Amine Protec>on
Aldehyde Deprotec>on
Internal decarboxyla>on
Amino acid catalyzed aldol
Mannich Cycliza>on
Ester reduc>on
Selec>ve Alcohol protec>on
Oxida>on to aldehyde
Alkene conversion and alcohol deprotec>on
Oxida>on to Aldehyde
Aldehyde to Alkene
Olefin Metathesis
Ester Reduc>on
Terminal alkene reduc>on
Conclusion
• 23stepsbutonly14chromatographicpurifica?ons
• Firstreportedenan?opureVallesamidineproduct
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