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Synthesis of Methyl-Protected (±)-Chlorizidine A
Jyoti P Mahajan1, Santosh B Mhaske1
1Division of Organic Chemistry, CSIR-National Chemical Laboratory , Pune 411 008, India.
Abstract:
The first total synthesis of the methyl-protected (±)-chlorizidine A has been achieved in 10 steps. Pd-catalyzed decarboxylative coupling and late-stage oxidation were utilized to construct the 5H-pyrrolo[2,1-a]isoindol-5-one scaffold. Samarium(II) iodide mediated Reformatsky reaction and intramolecular Mitsunobu reactions were efficiently applied for the synthesis of the 2,3-dihydropyrrolizine ring system. Chlorizidine A is highly prone to degradation; hence, methyl-protected (±)-chlorizidine A was prepared.
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