A variation of the Pictet-Spengler reaction via a sequential reduction-cyclization reaction of N-acylcarbamates: synthesis of 1-substituted tetrahydroisoquinoline derivatives |
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| Authors: | Chutima Kuhakarn Nattakan Panyachariwat |
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| Institution: | a Chulabhorn Research Institute, Vipavadee Rangsit Highway, Bangkok 10210, Thailand
b Department of Chemistry, Faculty of Science, Mahidol University, Bangkok 10400, Thailand |
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| Abstract: | A new variation of the Pictet-Spengler reaction for the synthesis of 1-substituted tetrahydroisoquinoline derivatives has been developed. The reaction employs the reduction of N-acylcarbamates by DIBAL-H followed by simultaneous cyclization mediated by BF3·OEt2. The synthetic potential of this method has been illustrated by the synthesis of the tetrahydroisoquinoline alkaloids, (±)-xylopinine, (±)-laudanosine, (±)-8-oxo-O-methylbharatamine, and (±)-isoindoloisoquinolone. |
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